Location: Sarasota
Do Not Show Listings
111 GOLDEN GATE PT #802PH, SARASOTA, FL 34236
$25,00033 Days on yellowkey MLS ID: A4696851
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3527 Built: 2024Community: EvolutionSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year:
Middle School: Booker Middle
Remarks: Experience the pinnacle of WATERFRONT LUXURY in DOWNTOWN SARASOTA's largest and most exclusive penthouse residence at THE EVOLUTION, a boutique community designed by architect MARK SULTANA, DSDG. This one-of-a-kind, TOP-FLOOR PENTHOUSE spans 3,527 SF of interior living plus 562 SF of wraparound TERRACE SPACE across THREE generous balconies for endless possibilities of indoor/outdoor living. Offering FOUR BEDROOMS plus a DEN and 4.5 BATHS, this residence provides the comfort of a single-family home with the elegance of HIGH-RISE LIVING. Sweeping NORTH, EAST, and SOUTH WATER VIEWS showcase SARASOTA BAY, the GULF, MARINA, and the CITY SKYLINE. FLOOR-TO-CEILING WINDOWS fill the home with natural light and allow year-round coastal breezes, and designer LUTRON ELECTRONIC SHADES grace each window, allowing privacy with ease. Interior features include ONYX QUARTZ COUNTERTOPS, PORCELAIN TILE SLABS, oversized PORCELAIN FLOORING, DESIGNER LIGHT FIXTURES, and CUSTOM EUROPEAN CABINETRY in the kitchen, baths, and closets. The PRIMARY SUITE features SILK WALLPAPER, and a SPA-INSPIRED BATH with dual sinks, a freestanding soaking tub, and onyx quartz and porcelain slab finishes. The CHEF'S KITCHEN includes WOLF APPLIANCES, sub-zero fridge-freezer with filtered water feature, induction cooktop, steam over, built-in coffee station, a wine refrigerator, and a HIDDEN WALK-IN PANTRY. Imported European fixtures complete with space. Enjoy THREE WRAPAROUND TERRACES for ALFRESCO DINING, YOGA, or SUNSET COCKTAILS. The unit includes a DEEDED PRIVATE TWO-CAR GARAGE and is MOVE-IN READY with every upgrade imaginable. Community amenities at THE EVOLUTION include a POOL WITH OUTDOOR KTICHEN, FITNESS CENTER, YOGA ROOM, SAUNA, CLUB ROOM, and a ROOFTOP TERRACE with PANORAMIC VIEWS, OUTDOOR LOUNGE SPA, and FIREPLACE. With only 20 RESIDENCES, this is a rare opportunity to live in one of Sarasota's most exclusive penthouses. Schedule your private tour today and experience the ultimate in penthouse living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
446 CANAL RD #5, SARASOTA, FL 34242
$2,450833 Days on yellowkey MLS ID: A4605587
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 680 Built: 1975Community: Twin BanyanCondo
Elementary School: None
High School: None
Middle School: None
Remarks: This is a short term (weekly) rental. Listing reflects peak season weekly rate. Discover Key Lime Retreat, an end-unit condo perfectly situated in the heart of Siesta Key. This delightful getaway combines comfort with modern style, ideal for families or a group of friends. Tucked away in a tropical garden setting, you'll enjoy access to a community pool, perfect for a refreshing dip. Everything you need is just a short walk away, from the pristine sands of Siesta Key Beach to vibrant shopping and delicious dining options. Inside, you'll find a thoughtfully designed space. The luxurious primary bedroom features a king-sized bed, while the guest bedroom is equipped with a twin bed plus a bunk bed, comfortably accommodating everyone. A newly updated bathroom offers a fresh space for relaxation, and the brand-new, fully equipped kitchen boasts modern appliances for all your culinary adventures. Nestled in a quiet building of just six units, Key Lime Retreat offers a serene escape. Step out onto your private front patio overlooking the garden and pool, a tranquil spot to savor your morning coffee or read a good book during the evening sunset. Whether you're here to explore or simply unwind, Key Lime Retreat promises a memorable and peaceful stay.
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
4645 TOWER HILL LN #2521, SARASOTA, FL 34238
$1,85094 Days on yellowkey MLS ID: A4689459
REDUCED by $100 (5.1%) on 06/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1310 Built: 1998Community: Stoneybrook Arbor Greens 1Condo
Remarks: Stoneybrook Golf and Country Club, Available NOW! Spectacular 2/2 Plus Den. Split Plan ready for new family! Amazing preserve view from back terrace, very Private. Community features are too many to list. Includes 1 covered parking space and a storage shed. The Arbor Greens heated pool and tennis court is just around the corner from the unit. There is no elevator in this building. A social membership can be transferred and includes access to the main heated lap pool, fitness center, newly redecorated clubhouse offering fine or casual dining, and all club activities, such as mahjong, yoga, water aerobics, cards, trivia, and more. Stoneybrook is a gated community centrally located close to Siesta Key, Costco, many shops and restaurants, and borders the Legacy walking and biking trail. Country club living at its finest. Available long term with easy move in.
Listing is courtesy of: A STEP ABOVE R. E. & MGMT INC. (941-342-6410)
Listing Agent: Kimberly Kay (941-342-6410)
1503 CLOWER CREEK DR #HA262, SARASOTA, FL 34231
$2,25053 Days on yellowkey MLS ID: A4694455
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1320 Built: 1979Community: Pelican Cove XvSpa: YesCondo
Remarks: ***AVAILABLE JUNE 1, 2026 THROUGH NOVEMBER 30, 2026*** TURN KEY FURNISHED...Wait until you see the view of the bay, amazing birds flying, fish jumping and the boats are all fantastic to watch from the privacy of your home. Located near the swimming pool, this 3 bedroom, 2 bath condo has the room to entertain or for family stop in for a few days. Pelican Cove is a gated community abounding with amenities, including a low cost 86-slip boat harbor, kayak and canoe launch, six heated swimming pools, hot tub, three clubhouses with walking trails, boardwalks and fishing gazebos. Take a class at Pelican Cove University or in yoga, tai-chi, water aerobics, painting or photography. Join one of the more than 37 clubs or photography, fiber arts, cycling, culinary arts, bridge, film and more. Or you can just relax at the evening jazz and classical music concerts, including concerts held harborside. Located on the lush grounds of the former Wilbanks Estate, Pelican Cove is hidden away yet minutes from everything! Come see for yourself!
Listing is courtesy of: AUDREY RAIN RENTALS, INC (941-487-7162)
Listing Agent: Anthony Deluca (941-685-6001)
8625 MIDNIGHT PASS RD #506B, SARASOTA, FL 34242
$2,750135 Days on yellowkey MLS ID: A4684215
REDUCED by $600 (17.9%) on 05/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1222 Built: 1970Community: Bay Tree ClubCondo
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Available May 15 through October 31, 2026, at a newly reduced rate of just $2,300 per month! November and December are available for $2,750 per month, and January is available for $5,000. Also available as an annual rental for $3,350 per month. Enjoy private access to the soft white sands and tranquil beauty of Turtle Beach on Siesta Key from this beautifully furnished 5th-floor penthouse. Offering picturesque bay and treetop views, this move-in-ready residence is located within one of South Siesta Key's most desirable Gulf-to-Bay communities. Designed for effortless coastal living, the light-filled interior features an open split-bedroom floor plan and tile flooring throughout. The updated kitchen showcases granite countertops, additional cabinetry, and ample workspace, while both bathrooms have been refreshed with stylish new vanities. Take in sweeping bay views from the living area, or enjoy the rare luxury of a privately owned beachside cabana—perfect for storing beach chairs, umbrellas, and all your seaside essentials while keeping Siesta Key's famous white sand where it belongs. Situated in the quieter southern section of the Key, you'll enjoy a peaceful setting while remaining close to local restaurants, shopping, and island activities. Hop aboard the Froghopper or Free Ride Trolley to explore Siesta Key with ease. Bay Tree amenities include: Private beach access to Turtle Beach Two heated pools (beachside and bayside) Grilling and picnic areas Free boat slips for owners Kayak storage racks On-site management Reserved owner parking Ample guest parking Whether you're walking to nearby dining, kayaking on the bay, enjoying a sunset beach stroll, or simply relaxing and taking in the views, this exceptional property offers the best of both bayfront and beachfront living. Seasonal Rates: May 15 – October 31, 2026: $2,300/month November – December 2026: $2,750/month January 2027: $5,000/month Annual Rental Rate: $3,350/month Contact us today for availability and additional details.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
1750 BENJAMIN FRANKLIN DR #1D, SARASOTA, FL 34236
$12,00030 Days on yellowkey MLS ID: A4695528
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1403 Built: 1970Community: Key Tower SouthCondo
Remarks: AVAILABLE 2027 SEASON & 6/26 - 12/26. This is a rare, convenience-driven Gulf-front luxurious retreat that delivers uninterrupted Gulf views, architectural volume, privacy, security, and seamless access to every amenity. A spectacular coastal offering designed for those who value discretion, quality, and effortless living. Welcome to a true turnkey coastal lifestyle opportunity defined by peaceful beach mornings, fun island afternoons, and elegant downtown evenings all from one exceptional, move-in-ready residence! Experience elevated island living in this FULLY RENOVATED, BEACHFRONT two-bedroom, two-bath condominium residence offering over 1,400 living square feet on Lido Key in beautiful Sarasota, Florida. Reimagined from the studs and beyond, the entire unit features NEW installed electrical (including breaker panel), NEW hurricane impact windows and slider doors, NEW designer tile throughout, a BRAND NEW sleek kitchen with BRAND NEW Bosch appliances, complete BRAND NEW bathrooms, NEW interior paint on NEW drywall, NEW LG washer and dryer, and more! Every detail is freshly installed. The Key Tower South building has been thoughtfully transformed with fresh exterior paint (2025), with a completely renovated lobby (2025), a state-of-the-art fitness center (2025), a stylish social room (2025), and a newly added business center for more private meetings (2025). Direct Gulf views as well as views of the beach and pool area. The fully restored community pool (2025) and Shellcrete deck by SRQ Modern (2025) create a private coastal oasis featuring fob-only gated beach access, a convenient beach wash-down station (2025), an outdoor shower (2025), grilling areas, and ample lounge seating for entertaining or unwinding. Begin your mornings with peaceful beach walks, enjoy full beach days just steps away, and end your evenings with breathtaking sunset strolls along the shoreline. Just a short walk from your residence, St. Armands Circle offers an unmatched island lifestyle with upscale dining, bars/pubs, boutiques, cafés, and vibrant nightlife. Outdoor enthusiasts will love nearby South Lido Park and the scenic Ted Sperling Park Nature Trail, ideal for kayaking, nature walks, and tranquil views of Sarasota Bay. When you’re ready for culture and city energy, Downtown Sarasota is just minutes away over the John Ringling Causeway, offering theaters, art galleries, retail shopping, high-end waterfront dining, year-round events, and much more! The building has undergone a FULL-SCALE TRANSFORMATION, including a complete renovation of the lobby, elevators, fitness center, social room, mail room, and the pool and pool deck. The arrival experience has been elevated with newly enhanced sightlines and “grand view” moments as you enter, achieved through thoughtfully opened walls and the addition of modern glass partitions. Outdoors, the property has been refreshed with all-new lawn, landscaping, and irrigation, fully replaced for a clean presentation. The coastal lifestyle awaits you!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Brenda Cozy (941-350-4889)
5649 SUMMER SIDE LN #41B, SARASOTA, FL 34231
$1,925291 Days on yellowkey MLS ID: R4909979
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1125 Built: 1984Community: SummersideSpa: NoCondo
Remarks: Available for long term rent July 1, 2026 Charming fully furnished 2-bedroom, 2-bathroom condo in the heart of Sarasota, featuring a cozy layout with a spacious kitchen, large living room with sliding doors that open to a balcony connected to the master bedroom, in-unit washer and dryer, and a quiet location at the end of the subdivision away from street noise. Rent includes trash service, and residents enjoy access to a nicely renovated community pool, one assigned shaded parking space with additional parking available for a second car, and walkable access to Red Bug Slough Preserve with playgrounds, nature trails, and ponds. Conveniently located near the beach, shopping plazas, and restaurants, this condo is available for long-term lease (6+ months preferred) with flexible terms and the option for seasonal rental at a higher rate depending on the months.
Listing is courtesy of: OHL LLC (941-445-1841)
Listing Agent: William Ol (941-445-1841)
5555 ASHTON LAKE DR #5555, SARASOTA, FL 34231
$4,15031 Days on yellowkey MLS ID: A4696129
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1106 Built: 1990Community: Ashton Lakes 01 & 02Condo
Elementary School: Gulf Gate Elementary
High School: Riverview High
Remarks: Location, Location, Location. Only 3.5 miles to the world-famous Siesta Key Beach. Close to I-75, rte.41, shops, restaurants & hospitals. This is a 2-bedroom 2 bath unit, turnkey furnished, on the 2nd floor of a 3-story building, with a screened lanai and impressive view of the large Sunnyside Lake. Elevator access. Unit is bright and airy. Just unwind on the lanai and let the Florida wildlife entertain you. Den has a murphy bed as well. Ashton Lakes Community is located on 33 acres of luscious greenery with 4 lakes, 2 tennis courts with 4 pickleball courts, shuffleboard, clubhouse, grilling stations, 2 heated pools, one with lap lanes. Rent includes all utilities, basic cable and wi-fi. Cleaning $200, association approval $50, tax 13% and refundable security deposit of $1000. We are also connected to Merchants mart shopping center by a foot bridge. There are numerous stores such as ACE hardware, Dollar store, Hair & nail salon, restaurants, liquor store and the famous Detweiler's Farm Market. Please contact agent for viewing.
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Philip Abraham (941-441-6958)
5601 ROSEHILL RD #203, SARASOTA, FL 34233
$1,85052 Days on yellowkey MLS ID: A4694731
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 2002Community: Admirals WalkCondo
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: OPEN FLOOR UNIT TWO BEDROOMS 2 BATHS AND A LOFT THAT CAN BE USED AS AN OFFICE OR GUEST BEDROOM. CLOSE TO I-75, EASY DRIVE TO LAKEWOOD RANCH, UCT MALL, SHOPPING CENTERS CLOSE BY, EASY COMMUTE TO SIESTA KEY, GREAT RESTAURANTS NEARBY AND WAL MART NEARBY, GREAT SCHOOL DISTRICT, UNIT AVAILABLE AS SOON AS HOA APPROVAL.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Hector Gomez, Llc (941-321-7164)
800 BENJAMIN FRANKLIN DR #505, SARASOTA, FL 34236
$6,50032 Days on yellowkey MLS ID: A4695740
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1978Community: Lido AmbassadorCondo
Remarks: Imagine waking up to the pristine elegance and effortless comfort of a luxury resort, right in your own home. Completely rebuilt with an eye for detail, this stunning rental offers an uncompromising standard of living with top-tier finishes and premium furnishings throughout. It is the perfect coastal retreat for those who refuse to settle for anything less than exceptional. Nestled directly adjacent to the renowned Lido Beach Resort, your daily routine can easily include a gorgeous waterfront breakfast at the Drift Kitchen and Bar or sunset drinks at the neighboring Tiki Bar. A short, scenic stroll takes you directly to the iconic St. Armands Circle for boutique shopping, fine dining, and lively entertainment, while outdoor enthusiasts will love having kayak launches just two blocks away. When you want to explore the vibrant arts and culture scene of downtown Sarasota, it is a mere 3.5 miles from your doorstep. You can even leave the car at home, as a free shuttle bus conveniently stops right in front of the building every thirty minutes to make getting around an absolute breeze. AVAILABLE IMMEDIATELY.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jessie Hayre (201-723-2847)
5408 EAGLES POINT CIR #302, SARASOTA, FL 34231
$3,00037 Days on yellowkey MLS ID: A4695917
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1695 Built: 1990Community: Bayview Homes ISpa: NoCondo
Remarks: This beautiful unit provides panoramic Intracoastal Waterway views and beautiful sunsets from every room of this updated unit. Located on the third-floor in Eagles Point at The Landings. This community is one of Sarasota’s most desirable, gated communities. Siesta Key Beach, which has been named #1 beach in the USA and downtown Sarasota are just minutes away. The unit is very light and bright. The unit boasts brand-new, top-of-the-line impact windows and an expansive triple-glass impact sliding door, offering both peace of mind and stunning views over mangroves toward Siesta Key and the Gulf. The building’s common areas have also been upgraded with impact windows for added security. Your first impression when stepping through the front door into a great room with a very open floor plan. The flooring is luxury vinyl plank flooring, freshly painted and includes designer lighting throughout. The upgrades include quartz countertops, designer tile backsplash, newer stainless steel appliances, lots of cabinetry, and an island with wine and beverage refrigerator, perfect for entertaining. The primary suite includes double glass doors, a private sitting or office area, dual walk-in closets, and a spa-inspired bath featuring double vanities and a large walk-in shower. The guest bedroom and bath are positioned for privacy, with gulf-facing views sure to impress you and your visitors. The unit provides a lot of light throughout the entire area. Beautiful and peaceful views provide a relaxing atmosphere to relax and enjoy the moment. Additional amenities include a full indoor utility room, new washer & dryer (2021), new A/C with humidistat (2021), and water heater (2020). The unit includes under-building parking, an extra storage locker, storage for kayak or paddleboard, bike room access, and plenty of guest parking. Eagles Point residents enjoy a private pool and grill area, plus membership in The Landings Racquet Club, featuring Har-Tru tennis courts, pickleball, junior Olympic lap pool, spa, fitness center, library, and social activities. Enjoy the mangrove-lined walking paths, fishing gazebo, kayak launch on the Intracoastal, and lush tropical surroundings, all of this is just minutes from downtown Sarasota, fine dining and shopping. If looking for a great location, luxury lifestyle, this is one place you must see. Unit is available furnished or unfurnished. Pets are allowed, 30lbs or less with a pet deposit. No commercial vehicles, motorcycles, RV's or trailers are allowed. No Smoking. Tenant to verify all room sizes.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Pat Gillum (941-809-3578)
6215 GREEN VIEW CIR #74, SARASOTA, FL 34231
$1,875113 Days on yellowkey MLS ID: A4687043
REDUCED by $75 (3.8%) on 06/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1405 Built: 1973Community: Village In The Pines 1Condo
Remarks: Move-in ready and freshly updated! This 2-bedroom, 2-bath furnished villa in the desirable 55+ community of Village in the Pines features a brand new A/C system and new flooring throughout. Everything you need is already here — furniture, washer and dryer included. Community amenities include a heated pool, clubhouse, and the convenience of lawn maintenance, water, and basic cable all included in rent. Located less than 5 miles from the world-famous shores of Siesta Key, with easy access to Gulf Gate shopping, dining, and everyday conveniences. Bring your suitcase and start living the Florida lifestyle today.
Listing Agent: Lee Brewer (941-724-3448)
1155 N GULFSTREAM AVE #1607, SARASOTA, FL 34236
$12,000300 Days on yellowkey MLS ID: A4664961
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1665 Built: 2017Community: Vue Sarasota BaySpa: YesCondo
Elementary School: Alta Vista Elementary
High School: Booker High
Remarks: Experience Sarasota at its most elevated in this exceptional 2-bedroom, 2.5-bathroom residence at The VUE, available now through December 2026. Fully furnished with top-of-the-line designer furniture, curated art, and refined finishes throughout, this luxury rental offers the rare opportunity to “test drive” the very best of Sarasota living before making a longer-term commitment to the area. From the moment you step off the private elevator, you are greeted by sweeping, unobstructed views of Sarasota Bay, Marina Jack, Bird Key, and the iconic John Ringling Bridge. Floor-to-ceiling windows and a spacious private terrace create a seamless indoor-outdoor living experience, offering breathtaking sunrises, glowing sunsets, and a front-row seat to the beauty of downtown Sarasota’s waterfront. Whether enjoying morning coffee, evening cocktails, or the Fourth of July fireworks, there is truly no view like The VUE. Inside, the residence has been thoughtfully refreshed with an elevated blend of sophisticated furnishings, statement art, and luxurious decor designed for comfort, style, and effortless entertaining. The gourmet kitchen features premium Sub-Zero and Jenn-Air appliances, sleek cabinetry, and generous space for preparing meals at home or hosting guests before a night out downtown. The primary suite serves as a private retreat, complete with stunning water views, a spa-inspired bathroom, and a spacious walk-in closet. Additional features include soaring 10-foot ceilings, elegant tile flooring, automatic blinds, and beautifully curated living spaces throughout. Life at The VUE is designed to be effortless. Residents enjoy valet parking, concierge service, 24-hour security, a resort-style pool and spa, a state-of-the-art fitness center, private elevator access, and resident activity and events. The neighboring Ritz-Carlton and Westin place world-class dining, hospitality, and amenities just moments away. Perfectly positioned in the heart of downtown Sarasota, this residence offers immediate access to the city’s best restaurants, arts, culture, boating, shopping, St. Armands Circle, Longboat Key, Lido Beach, and the Gulf Coast lifestyle that continues to attract discerning buyers and renters from around the country. This is more than a furnished rental. It is a luxurious introduction to Sarasota living, designed for those who value convenience, beauty, privacy, and a truly turn-key experience. Please note that pets and smoking are not permitted in this unit under any circumstances. Contact us today to schedule your private showing.
Listing is courtesy of: DANIELLE GLADDING & CO. REALTY (941-539-8535)
Listing Agent: Alison Kanter (941-306-9786)
33 S GULFSTREAM AVE #1001, SARASOTA, FL 34236
$3,00040 Days on yellowkey MLS ID: A4696088
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1055 Built: 1964Community: Gulfstream TowersCondo
Remarks: Location Location! Perched on the 10th floor of the iconic Gulfstream Towers, this beautifully maintained condominium offers breathtaking panoramic views of Sarasota Bay, the Gulf of Mexico and the vibrant downtown skyline. This light filled residence offers 2 bedrooms and 2 bathrooms with an open concept layout designed to maximize natural light and waterfront vistas. The updated kitchen showcases stainless steel appliances, solid surface countertops and ample cabinetry, flowing seamlessly into the spacious living and dining areas. Floor to ceiling window fame. spectacular water views. The master bedroom offers comfort and privacy, while the guest bedroom provides flexibility for visitors or a home office. Enjoy amenities in the building a waterfront heated pool, fitness center, library, secure building access, and covered parking. Located in the heart of downtown Sarasota the condo is just steps from the Bayfront, Marina , restaurants, shopping and the scenic John Ringling Causeway. Call today to schedule your showing.
Listing is courtesy of: MONARCH PROPERTY GROUP LLC (941-270-1675)
Listing Agent: Angela Bailey (941-270-1675)
3350 S OSPREY AVE #209A, SARASOTA, FL 34239
$1,85078 Days on yellowkey MLS ID: A4691461
REDUCED by $50 (2.6%) on 06/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1122 Built: 1969Community: Bermuda On OspreySpa: NoCondo
Remarks: Beautiful unfurnished 2-bedroom, 2-bath condo available for annual rental in the well-located Oasis on Osprey community in Sarasota. This second-floor residence offers elevator access, a spacious living and dining area, a well-appointed kitchen, two comfortable bedrooms, two full bathrooms, and a screened balcony for relaxing outdoor space. The community offers a pool, small fitness room, coin laundry, one assigned parking space, and guest parking subject to availability. The location is one of the strongest features of this condo. It is just minutes from Siesta Key, Southside Village, Sarasota Memorial Hospital, Hillview, Downtown Sarasota, shopping, dining, grocery stores, and everyday conveniences. The Crossings at Siesta Key is approximately two blocks away, making errands, restaurants, and services very convenient. This is a great option for someone looking for a clean, well-located annual rental west of Tamiami Trail with easy access to beaches, medical facilities, downtown Sarasota, and daily conveniences. Annual lease preferred. Unfurnished.
Listing Agent: Alberto Garcia (941-730-5205)
8370 WINGATE DR #724, SARASOTA, FL 34238
$4,300415 Days on yellowkey MLS ID: A4650369
REDUCED by $100 (2.3%) on 06/12/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1996Community: Pinestone At Palmer RanchCondo
Remarks: Available for the Season - December 20, 2026 - April 30, 2027. Three month minimum. This spacious 3 bedroom, 2 bath condo with a beautiful lake view in the sought after community of Pinestone At Palmer Ranch with all its amenities! This 1,604 sq. ft. condo unit is a "Chateau" model where the Primary bedroom, with a King bed and ensuite bathroom is on the 2nd floor! This unit is unique in its layout with an open floor plan. The kitchen, dining area and living room are open to relaxing views out the lanai where you can see the glistening water of Crockers Lake, trees and colorful sunsets. The two other bedrooms are on the main floor with Queen beds and small working desks and they share a full bathroom with tub and shower combined. One bedroom faces the water view and the other bedroom is on the opposite front side of the condo so each bedroom has privacy. This condo is furnished and the owner will consider renting it unfurnished. The condo has cooking utensils, pots and pans, coffee pot, toaster, microwave oven, stove top and oven, dishwasher, refrigerator and full size side by side washer and dryer, everything you need to move right in and enjoy the home and community. All potted plants have been removed from the condo. The Pinestone Community has a Clubhouse, fitness center, billiards room, 25 seat movie theater, Jr Olympic size pool with lap lanes, hot tub, two lighted tennis/pickleball courts and a 1/2 basketball court, shuffleboard, corn hole, bocce ball, two outdoor seating areas, one with a fire pit. Close to I-75 and Highway 41 (Tamiami Trail). Nearby is the Legacy Trail for walking or biking, close to shopping at Publix, Sprouts, Ulta, Costco, Lowes, CVS, Walgreens and local dining. Five miles to the Siesta Key South Bridge and a short drive to Siesta Beach, Turtle Beach, watersports with local shopping and dining in south Siesta Key and north in Siesta Key Village. Explore Downtown Sarasota and discover all the wonderful local restaurants and boutique shops. Sarasota is on the west coast of Florida which is considered the cultural coast. Sarasota is well know for Museums and Art galleries such as the John and Mable Ringling Museum, the Sarasota Art Museum, Art Center Sarasota, State of the Arts Gallery, Wyland Galleries, Marie Selby Botanical Gardens and many more to explore.
Listing is courtesy of: M&M PROPERTY MANAGEMENT GROUP (941-320-4287)
Listing Agent: Jana Nizny (941-735-6045)
4377 LONGMEADOW #7, SARASOTA, FL 34235
$2,00069 Days on yellowkey MLS ID: A4692700
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $190 (8.7%) on 05/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1182 Built: 1984Community: Woodland Grove/The MeadowsSpa: NoCondo
Elementary School: Gocio Elementary
Remarks: Welcome to your slice of paradise in The Meadows ?? This beautifully maintained 2-bedroom, 2-bath ground-floor END unit in Woodland Grove offers the perfect blend of comfort, light, and serene lakefront living. With extra windows on three sides, this corner residence is filled with natural light and showcases peaceful views of trees and a sparkling lake from your private screened lanai. Inside, you’ll find diagonal tile flooring throughout (no carpet) and a neutral color palette that complements any style. The spacious layout features a king-size bed in the primary suite, two twin beds in the guest room, and a walk-in closet in the primary. The primary bath includes a walk-in shower, while the guest bath offers a relaxing soaking tub. The kitchen is equipped with stainless steel appliances and an eat-in area with a 4-top table, plus a separate dining space with seating for six—perfect for entertaining. A large laundry room adds convenience, and assigned parking is included. Offered turnkey furnished (or unfurnished if preferred), this home is move-in ready and designed for easy Florida living. Step outside and enjoy a charming canopied wooden walkway leading to the neighborhood pool, surrounded by lush tropical landscaping. Woodland Grove is a peaceful enclave within The Meadows, known for its 14 miles of walking, biking, and nature trails, plus optional fee schedules for golf, tennis, pickleball, and fitness. ?? Prime location just minutes to: • Downtown Sarasota’s cultural scene • UTC shopping and dining • I-75 for easy travel • World-renowned Gulf beaches Additional Details: • Utilities are tenant responsibility • No overnight truck parking • Two-step application process required If you're looking for a bright, tranquil, and well-appointed rental in one of Sarasota’s most established communities—this one delivers.
Listing Agent: Amy Chapman (941-225-1500)
845 BENJAMIN FRANKLIN DR #302, SARASOTA, FL 34236
$3,25034 Days on yellowkey MLS ID: A4696614
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 756 Built: 1974Community: Presidential TheCondo
Remarks: BEACH LOVERS WANTED! You can experience the Lido Key lifestyle daily in this updated 1-bedroom + den 3rd floor Condo with pool and peakaboo Sarasota Bay views. Ideally located directly across from Lido Beach and a short walk to St. Armand Circle, Ted Sperling Park, and Lido Beach Park. Perfect for easy beach-to-door living!! With only 40 Units, this Boutique Community is your perfect hideaway. The property abounds with palm trees and exotic plants. There is elevator access or two sets of stairs. Recent Condo updates include custom reclaimed wood kitchen & bathroom cabinetry (from the Brooklyn Shipyard), newer appliances-stone tiled bathroom- air conditioning-hot water heater-and impact sliding doors. Being offered completely furnished (*except some artwork, antiques)- just bring your suitcases! The Bayrunner Trolley stops out front and is free. Enjoy Sarasota's extensive Arts, Restaurants and nightlife without ever worrying about parking after your day in the sun. Make an appointment to see this gem now.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Wayne Fastzkie (941-315-0442)
1255 N GULFSTREAM AVE #1101, SARASOTA, FL 34236
$7,00033 Days on yellowkey MLS ID: A4695734
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1923 Built: 1982Community: Bay PlazaSpa: NoCondo
Remarks: Virtually Staged. Live the ultimate Sarasota lifestyle at 1255 N Gulfstream Ave #1101, a rarely available largest end unit in Bay Plaza—originally designed as a full 3-bedroom layout. This renovated 3-bedroom, 2-bath, 11th-floor Sarasota condo is available for lease in downtown Sarasota, Florida. Perfectly situated in downtown Sarasota, this bright and airy residence offers sweeping views of Sarasota Bay, Marina Jack, and the vibrant city skyline. Floor-to-ceiling hurricane-impact windows and recently installed hurricane-rated sliding glass doors provide stunning natural light, energy efficiency, and quiet comfort. The open-concept layout seamlessly connects a spacious living area, dining area, and a modern kitchen with sleek quartz countertops—ideal for both entertaining and everyday living. Recent upgrades include fresh interior paint, stylish new glass shower doors and vanities in both bathrooms, updated ceiling fans and light fixtures, expanded storage with a wine cooler in the kitchen, and custom closet systems throughout. Step outside onto one of four private balconies to enjoy spectacular sunrises, sunsets, and front-row seats to Sarasota’s signature fireworks celebrations, including the Fourth of July at Marina Jack. As a resident of Bay Plaza, you’ll enjoy premium amenities, including secure two-car garage parking, 24/7 valet parking, EV charging stations, and attentive concierge services. Unwind at the heated pool, relax in the spa, or stay active in the state-of-the-art fitness room with sauna and steam room. There’s also a shaded entertainment deck, outdoor grilling area, extra storage, and onsite maintenance staff for your convenience and peace of mind. Perfectly positioned in the heart of downtown Sarasota, Bay Plaza places you within easy reach of trendy restaurants, boutiques, Bayfront Park, Marie Selby Botanical Gardens, Florida Studio Theater, Sarasota Opera House, Whole Foods, the Saturday Farmers Market, and Sarasota’s vibrant cultural scene. Enjoy quick access to St. Armands Circle, Longboat Key, and the city’s stunning beaches.
Listing is courtesy of: CANDY SWICK & COMPANY (941-954-9000)
Listing Agent: Candy Swick (941-376-9000)
111 S PINEAPPLE AVE #1103, SARASOTA, FL 34236
$8,00035 Days on yellowkey MLS ID: A4696491
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1600 Built: 2019Community: Mark SarasotaSpa: YesCondo
Remarks: Virtually Staged. Experience elevated downtown living at The Mark Sarasota in this stunning 2-bedroom, 2-bath luxury condominium with approximately 1,600 square feet of sophisticated living space. Offered at $8,000 per month, rent includes electricity, water, and sewer. Built in 2019, this newer-construction residence showcases a bright, open floor plan with soaring 10-foot ceilings and beautiful views of downtown Sarasota. The thoughtfully designed split-bedroom layout offers privacy and functionality, while a den featuring a built-in fireplace provides the perfect space for a home office, media room, or additional living area. The chef’s kitchen is appointed with premium Miele appliances, sleek cabinetry, and high-end finishes, creating an elegant space for entertaining and everyday living. Additional upgrades include a hidden speakeasy bar, reverse osmosis water filtration system, in-unit laundry room, and climate-controlled storage. Residents of The Mark enjoy resort-style amenities including a saltwater pool, state-of-the-art fitness center, yoga studio, spin room, billiards room, fire pit lounge, grilling areas, and 24-hour concierge service. Ideally located in the heart of downtown Sarasota, this residence offers a truly walkable lifestyle just steps from the Sarasota Farmers Market, Whole Foods, Sarasota Opera House, Florida Studio Theatre, Selby Public Library, Marina Jack, Bayfront Park, world-class dining, boutique shopping, and cultural attractions. Enjoy luxury, convenience, and vibrant downtown living in one of Sarasota’s most sought-after addresses.
Listing Agent: Angela Adams (941-809-9760)
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