Location: Sarasota, 34239
Do Not Show Listings
1738 SIESTA DR, SARASOTA, FL 34239
$6,50026 Days on yellowkey MLS ID: A4692339
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2131 Built: 2013Community: GranadaSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year:
Middle School: Brookside Middle
Remarks: Available June 1st, this newer (2013) “West of Trail” pool home offers an ideal opportunity to get settled ahead of the upcoming school year in the highly regarded Southside Elementary district, just a short bike ride away. Offered at $6,500/month with an annual lease preferred (6-month considered), the home provides flexibility with furnishings — available furnished or unfurnished. Elevated 22 feet above sea level in an X flood zone, it delivers both peace of mind and easy coastal living with a thoughtful layout featuring 4 bedrooms along with a versatile downstairs bonus space ideal for a media room, playroom, or additional lounge area. All bedrooms located on the 2nd level with bonus room, great room and kitchen on the main. Southern exposure fills the coastal-casual great room and updated kitchen with natural light, overlooking a private saltwater pool and lush tropical setting. Pocketing sliders create seamless indoor-outdoor living, perfect for relaxing or entertaining beneath the flowering plumeria. Designed for low-maintenance living, the property includes artificial turf, mature landscaping, and multiple outdoor gathering areas, with pool care, lawn care, and internet included in the rent. A two-car garage features a Tesla Level 2 EV charger and space for bikes and beach gear. Located in the historic Granada neighborhood with easy access to Southside Village dining, including Shakespeare’s Craft Beer & Gastro Pub, and just 10 minutes to both Siesta Key and Downtown Sarasota. Pets considered on a case-by-case basis with owner approval and deposit.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Ryan Adamson, Pa (941-713-9234)
3001 BEE RIDGE RD #117, SARASOTA, FL 34239
$1,2001 Day on yellowkey MLS ID: A4695322
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 560 Built: 1964Community: South GateSpa: NoCondo
Elementary School: Wilkinson Elementary
Remarks: One or more photo(s) has been virtually staged. Don't miss this first-floor 1BR, 1BA apartment offering a comfortable and convenient layout! The open-concept living and dining area, complete with wood plank laminate flooring, creates an inviting space for your invited friends and family. The kitchen comes equipped with a refrigerator and range, and plenty of counter and cabinet space for all your meal prepping needs. Completing the apartment is a roomy bedroom with carpet flooring, a bathroom, and outdoor access to a paved patio space. Centrally located off Bee Ridge, you will be minutes away from shopping, restaurants, and entertainment, and just a short drive to one of the best beaches in the country! Ridge Garden offers residents assigned parking, a sparkling community pool, on-site laundry, a sun deck, community grills, and a dog park. PMI Southwest Florida has partnered with Obligo to provide a security deposit alternative to qualified renters! ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee Pets: Pet(s) considered, up to 35 lbs. $250 Non-refundable pet fee Included: Trash service, lawn care, and pest control THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)
Listing Agent: Mj Loparco (941-216-0022)
1537 SIESTA DR, SARASOTA, FL 34239
$18,50024 Days on yellowkey MLS ID: A4692741
REDUCED by $1,500 (7.5%) on 05/29/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3727 Built: 2023Community: Sunset Bay SubSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to Siesta by the Bay! This turnkey luxury home features 4 ensuite bedrooms, water views of the bay, pool bath and half bath, outdoor shower, outdoor kitchen, heated pool, putting green, and 3 car garage. Enjoy a private backyard with an expansive outdoor dining area and bar with multiple areas to exercise and lounge. Located near the Siesta Key North bridge, you’re minutes from world famous beaches, downtown Sarasota, Hillview Shopping Plaza, Sarasota Memorial Hospital, fine dining, and many more popular activities that Sarasota has to offer. Home is available for short-, mid-, and long-term rental. Rates vary based on season.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Tina Ellis (512-550-1117)
2541 FLOYD ST, SARASOTA, FL 34239
$2,00057 Days on yellowkey MLS ID: A4688717
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 916 Built: 1962Community: Rustic LodgeSingle Family
Elementary School: Alta Vista Elementary
Remarks: Available for immediate move in. 2 bed 1 bath house with fenced in backyard located in the Arlington Park neighborhood of Sarasota. Updates include newer appliances, ceramic tile floors throughout, granite counter tops, kitchen cabinets, lights, ceiling fans and fixtures. It is conveniently located within walking distance to Sarasota Memorial Hospital. A quick drive to Lido Key Beach & St. Armand's Circle and only 15 minutes to the pristine beaches of "world renowned" Siesta Key. A short 10-minute walk will take you to Arlington Park and Aquatic Complex, which features several pools, tennis & racquetball & basketball courts, playground, gymnasium, cycling and fitness center. Please call to schedule your showing today! Rent includes lawn care and pest control.
Listing is courtesy of: O'STEEN GROUP INC (941-527-4227)
Listing Agent: Jonathan O'Steen (941-704-7036)
2216 WEBBER ST #C, SARASOTA, FL 34239
$1,55035 Days on yellowkey MLS ID: A4688118
REDUCED by $50 (3.1%) on 05/28/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 650 Built: 1956Community: Long MeadowSingle Family
Remarks: Totally redone, 2 bedroom, 1 bath and a den house available. New kitchen, new paint, appliance, blinds etc. Back and side yard are fully fenced. Near Southside Elementary School, Southside Village shops and restaurants. A quick walking path to Westfield Siesta Key mall and Shops at Siesta Row. Near Sarasota Memorial Hospital and about 2-3 miles from downtown Sarasota.
Listing is courtesy of: MARLENE LANCASTER REALTY (941-374-7700)
Listing Agent: Sarah Massey, Pa (941-374-2525)
3700 S OSPREY AVE #221, SARASOTA, FL 34239
$1,74551 Days on yellowkey MLS ID: A4689484
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1053 Built: 1979Community: Plaza GardensCondo
Remarks: Ideally situated close to downtown Sarasota and Sarasota Memorial Hospital. This non-street facing second-floor end unit, providing extra privacy has 2 bedrooms and 2 baths, private screened lanai and assigned parking. The building is equipped with a convenient elevator for easy access to your unit. Publix grocery store is just across the street and Siesta Key beach is over the bridge 5 minutes away. Don't miss this opportunity to live in a prime Sarasota location!
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Maureen Plichta (941-812-5799)
3001 BEE RIDGE RD #124, SARASOTA, FL 34239
$1,20016 Days on yellowkey MLS ID: A4693660
0 Days Off yellowkey (back on 5/28/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 560 Built: 1964Community: South GateSpa: NoApartment
Remarks: One or more photo(s) has been virtually staged. Move-in Specials: Only $700 Security Deposit! Apply before June 1st and get half off your Application Fee. This first floor, 1BR, 1BA end unit is just what you've been looking for! The kitchen is adorned with bright, hardwood cabinets and includes a refrigerator, range, and microwave for all your cooking needs. The open living and dining area offers plenty of space to host friends and family and stays brightly illuminated by the sliding glass doors that lead onto the covered paved patio space. The bedroom down the hall, and a sizeable bathroom complete the remainder of this unit. Centrally located off Bee Ridge, you will be minutes away from shopping, restaurants, and entertainment, and just a short drive to one of the best beaches in the country! Ridge Garden offers residents assigned parking, a sparkling community pool, on-site laundry, a sun deck, community grills, and a dog park. PMI Southwest Florida has partnered with Obligo to provide a security deposit alternative to qualified renters! ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee Pets: Pet(s) considered, up to 35 lbs. $250 Non-refundable pet fee. Included: Trash service, lawn care, and pest control THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
1865 ORCHID ST, SARASOTA, FL 34239
$7,500757 Days on yellowkey MLS ID: A4609514
REDUCED by $500 (6.3%) on 05/28/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2252 Built: 1953Community: Poinsettia Park 2Single Family
Remarks: Welcome to tropical paradise! This stunning home away from home offers the perfect blend of relaxation and fun for all. Take a dip in the brand-new saltwater pool and spa, wind down by the cozy firepit. With spacious bedrooms, a fully equipped kitchen, and cozy living areas, you'll have everything you need! Distance from Siesta Key Beach: 4.5 miles Distance from downtown Sarasota: 2.7 miles Distance from St. Armand Circle and Lido Key: 5.4 miles This beautiful 4-bedroom, 3-bathroom turnkey furnished property offers a spacious and open concept layout. The open kitchen seamlessly flows into the dining space and living room, creating the perfect space for entertaining and spending quality time with family and friends. One of the highlights of this property is the stunning pool and spa, where you can enjoy tropical drinks and unwind after a long day. Surrounding the pool are comfortable sun loungers, where you can relax and soak up the sun. There’s plenty of room for the whole family! Available for short/mid- and long-term rental.
Listing is courtesy of: COMPASS FLORIDA LLC (305-851-2820)
3755 S SCHOOL AVE #41, SARASOTA, FL 34239
$2,05036 Days on yellowkey MLS ID: A4691238
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1972Community: Sunland AptsCondo
Remarks: 55+ Community. LIMITED TIME DISCOUNT ON FIRST 3 MONTHS OF RENT (INQUIRE FOR DETAILS). VERY LOW MOVE IN COSTS! ONLY FIRST MONTH RENT AND A $500 SECURITY DEPOSIT REQUIRED. LEASE OPTION WOULD BE CONSIDERED. Owner pays the association fees, and rent includes cable, water, sewer, trash, and more. Beautifully updated and move-in-ready condo located in the heart of Sarasota, just minutes from world-famous Siesta Key Beach. This 2-bedroom, 2-bath residence offers a bright, open layout with abundant natural light and a comfortable flow for everyday living. The interior features updated flooring, neutral finishes, and a functional kitchen with modern cabinetry, ample counter space, and a breakfast bar that opens to the main living area. The spacious primary suite includes an en-suite bathroom, walk-in closet, and private access to the lanai, while the guest bedroom is well-positioned for privacy with generous closet space. Both bathrooms have been updated with clean, modern finishes. Enjoy peaceful views, creating the perfect setting to relax or unwind. Additional features include sliders, elevator access, and nearby storage and laundry facilities. Located in a well-maintained community with convenient access to shopping, dining, and entertainment, as well as close proximity to downtown Sarasota and the beaches.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
1891 PROSPECT ST, SARASOTA, FL 34239
$2,800124 Days on yellowkey MLS ID: A4679960
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1091 Built: 1950Community: Floyd & Cameron SubSingle Family
Remarks: Welcome to this charming West of the Trail 2-bedroom, 1-bathroom home Fully furnished. This cozy gem offers a blend of comfort and convenience. Inside, you’ll love the abundance of natural light, updated kitchen with stainless steel appliances, and ceiling fans throughout for added comfort. The home also features air conditioning, central heating, and an inside laundry room complete with a washer and dryer. An enclosed sunroom provides the perfect flexible space—think home office, dining room, reading nook, or art studio. Step outside to the deck, where you can sip your morning coffee under the shade of mature trees and beautiful canopied oaks. The carport offers a small storage area for your outdoor essentials, and the home is pet-friendly too! Situated in an unbeatable location, you’re minutes from Sarasota Memorial Hospital, Southside Village’s vibrant dining and shopping scene, and the cultural offerings of Downtown Sarasota and Sarasota Bay. Plus, explore Florida’s famous coastline with quick access to Siesta Key Beach, Lido Beach, and St. Armands Circle. Lawn care is included in rent—don’t miss this opportunity. Call today to schedule your showing and make this home yours! Note: This pet-friendly home is move-in ready—don’t wait, it won’t last long!
Listing Agent: Beth Harris (941-321-7148)
3001 BEE RIDGE RD #121, SARASOTA, FL 34239
$1,2003 Days on yellowkey MLS ID: A4694957
Remarks: This first floor 1BR, 1BA apartment is ready for you to call home! The kitchen features ample storage space, granite counter tops, and stainless-steel appliances including a refrigerator, range, and microwave. The open concept floorplan is the perfect place to host guests, featuring a sliding glass door off the living area that opens out onto your paved patio space! The bedroom is complete with a ceiling fan, and a large closet for extra storage, and includes plenty of space to make this room uniquely yours! A roomy bathroom down the hall completes the remainder of this unit. Centrally located off Bee Ridge, just minutes away from shopping, restaurants, and entertainment, and just a short drive to one of the best beaches in the country! Ridge Garden offers residents assigned parking, a sparkling community pool, on-site laundry, a sun deck, community grills, and a dog park. PMI Southwest Florida has partnered with Obligo to provide a security deposit alternative to qualified renters! ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee Pets: Pet(s) considered, 35lbs max. $250 Non-refundable pet fee Included: Trash service, lawn care, and pest control THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
3425 FAIRVIEW DR, SARASOTA, FL 34239
$2,950108 Days on yellowkey MLS ID: A4682215
REDUCED by $50 (1.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 1965Community: South GateSingle Family
Remarks: ANNUAL FURNISHED 3 BEDROOM PLUS DEN POOL HOME AVAILABLE FOR ANNUAL LEASE IN SOUTH GATE! (Owner will consider unfurnishing the home.) The fully updated home has a beautiful kitchen with granite counters and stainless-steel appliances, modern bathrooms featuring matching granite, a walk-in closet in the primary bedroom, an open floor plan with a spacious great room adjacent to the kitchen, and a bright office overlooking the pool. The expansive covered outdoor area provides shade and an inviting spot for gatherings with friends and family, while the large, screened pool offers ample space for swimming laps or simply relaxing in the sun. The split floor plan ensures privacy, with the master suite separated from the guest bedrooms and office. The excellent location provides easy access to downtown Sarasota, shopping, dining, Siesta Key Beach, Lido Key, and the Legacy Trail. Lawn and pool maintenance included.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
Listing Agent: Alex Lane (941-960-3080)
3001 BEE RIDGE RD #219, SARASOTA, FL 34239
$1,200138 Days on yellowkey MLS ID: A4677956
REDUCED by $200 (14.3%) on 04/14/2026
Remarks: One or more photo(s) has been virtually staged. Move-in Specials: Only $700 Security Deposit! Apply before June 1st and get half off your Application Fee. This second-floor apartment features an open-concept layout. With 1BR and 1BA, it offers a comfortable and efficient living space. The kitchen is perfectly sized and comes equipped with a refrigerator and range. Neutral paint tones and tile flooring throughout create a clean, versatile backdrop that's easy to personalize. The bedroom sits conveniently across from the bathroom and includes a large closet for convenience. Enjoy additional storage space with a utility closet located in the hallway for extra storage. Picture yourself sitting out on your private balcony, enjoying the nice warm breeze after a long day and catching a glimpse of those infamous Florida sunsets. *Virtually Staged photos included.* Centrally located off Bee Ridge, you will be minutes away from shopping, restaurants, and entertainment, and just a short drive to one of the best beaches in the country! Ridge Garden offers residents assigned parking, a sparkling community pool, on-site laundry, a sun deck, community grills, and a dog park. PMI Southwest Florida has partnered with Obligo to provide a security deposit alternative to qualified renters! ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee Pets: Pet(s) considered, 35lbs max. $250 non-refundable pet fee. Included: Trash service, lawn care, and pest control THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
3364 ESPANOLA DR, SARASOTA, FL 34239
$6,000158 Days on yellowkey MLS ID: L4958067
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 1969Community: Frst Lakes Country Club EstatesSingle Family
Remarks: SHORT-TERM RENTAL – FULLY FURNISHED POOL HOME IN FOREST LAKES SARASOTA. Gorgeous, fully renovated 3-bedroom, 2-bathroom pool home with a 2-car garage, available for flexible lease terms of 1, 3, 6, or 9 months (minimum 30 days). This move-in-ready home features an open floor plan, updated kitchen with stainless steel appliances and granite countertops, spacious primary suite, and a private screened pool—perfect for enjoying Florida living. Conveniently located near shopping, dining, and just minutes from Siesta Key Beach. Rent includes: electricity, water, internet, lawn care, pest control, and pool maintenance. Tenant occupied – Available 06/15/2026 Furnished | Short-term rental | Minimum 30-day stay Please note: The advertised rate of $6,000/month applies to longer-term stays (typically 6+ months). Short-term and peak-season rates may be higher. Call for availability and detailed pricing.
Listing is courtesy of: HIGDON HOMES REALTY LLC (863-209-2543)
Listing Agent: Fatma Higdon (863-209-5243)
1850 WEBBER ST, SARASOTA, FL 34239
$15,00014 Days on yellowkey MLS ID: A4693021
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4755 Built: 2026Community: Poinsettia Park 2Spa: YesSingle Family
Remarks: One or more photo(s) has been virtually staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Dyrk Dahl (941-320-7373)
3350 S OSPREY AVE #209A, SARASOTA, FL 34239
$1,90033 Days on yellowkey MLS ID: A4691461
REDUCED by $50 (2.6%) on 05/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1122 Built: 1969Community: Bermuda On OspreySpa: NoCondo
Remarks: Beautiful 2-bedroom, 2-bath condo located just minutes from Siesta Key Beach (Shell Rd access approx. 5 minutes) and Siesta Key Village (approx. 8 minutes), nestled in the well-established Oasis at Osprey community. Situated on the second floor with convenient elevator access, this inviting residence offers the perfect blend of comfort and location for your Sarasota stay. The condo features a well-appointed kitchen, spacious living and dining areas, two comfortable bedrooms, and two full bathrooms, along with a screened balcony ideal for relaxing and enjoying the Florida lifestyle. Community amenities include a pool, small fitness room, coin laundry, and one assigned parking space, with additional guest parking available (subject to availability). Ideally located just two blocks from The Crossings at Siesta Key, you’ll be surrounded by shopping, dining, and everyday conveniences. With close proximity to Siesta Key Beach, Southside Village, Downtown Sarasota, Sarasota Memorial Hospital, Hillview area, and easy access to I-75, this West of the Trail location truly offers it all. Enjoy the best of Sarasota living—beaches, dining, and vibrant city life—all just minutes from your door.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Alberto Garcia (941-730-5205)
1828 GROVE ST, SARASOTA, FL 34239
$4,5008 Days on yellowkey MLS ID: A4694432
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1559 Built: 1925Community: South Poinsettia ParkSingle Family
Remarks: Great West of Trail home that has been updated with modern conveniences while retaining the original charm of the classic Florida bungalow. The primary suite addition has a huge walk-in closet and large spa like bath with double sinks and walk in stepless oversized shower. The split bedroom plan has the second bedroom and bath off the living room. The updated kitchen is open to the living area and includes granite countertops, a generous sized countertop with seating area, a gas range plus a door to the side yard if you want to barbecue. An additional room that can be used as an office and an interior laundry room provide added conveniences. At the end of the brick paved driveway is a large separate 2 car garage and an additional brick paved area. Southside Village is nearby with popular shops and restaurants to enjoy.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
1773 HARMONY LN, SARASOTA, FL 34239
$5,00011 Days on yellowkey MLS ID: A4692810
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1098 Built: 1953Community: Bay View Heights AddSingle Family
Remarks: OFF SEASON RENTAL ONLY! This west of Trail, west of Osprey home rests on the edge of Cherokee Park on a canopied street in one of the most sought-after locations in all of Sarasota—situated between the North Bridge to Siesta Key and downtown. Fully turnkey furnished and well-appointed, this is a charming two bed/two bath home perfect for experiencing the laid back Florida lifestyle. Walk to Morton's Market in Southside Village, Southside Elementary, Selby Gardens, or Bayfront Park. Be perfectly close to the bay, while not in a flood zone. Rays of sunshine filter through the tree canopy and into the windows, illuminating a bright and open floor plan. The split floor plan features each bedroom with its own bath on separate sides of the home. Enjoy spending evenings on the back patio amidst mature landscaping and dining al frescoat the outdoor table with umbrella for shade in the fully fenced and private yard.This Sarasota rental is located in the best area of Sarasota. Take a stroll down the street to watch the sunset over the water or enjoy a bike ride and explore this magical neighborhood. OFF SEASON RENTAL ONLY. AVAILABLE JUNE THROUGH NOVEMBER.
Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)
Listing Agent: Bridget Gennett (941-224-4315)
3835 ALMERIA AVE #C3, SARASOTA, FL 34239
$1,90011 Days on yellowkey MLS ID: A4694273
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 925 Built: 1970Community: Westchester ICondo
Remarks: Near the north Siesta Key Bridge and bay. Amazing location. Walk to see sunset over Sarasota Bay. Unfurnished. 1 car covered parking. Minutes to Siesta Key Beach. Minutes to Hillview and Southside. Part of Southside Elementary school district. Dead end street. Walk to restaurants and shopping. top floor of a 2 story building with a big relaxing Lanai Covered Parking. In unit laundry Quiet location.
Listing is courtesy of: SUNCOAST LUXURY PROPERTIES (941-504-5348)
Listing Agent: Richard Dear (941-504-5348)
1726 FLOYD ST, SARASOTA, FL 34239
$8,000262 Days on yellowkey MLS ID: A4664721
Bed: 3 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1461 Built: 1954Community: Midwood ManorSingle Family
Remarks: SEASONAL RENTAL - Available June 1, 2026 -3/BR; 1.5/baths Renovated, beautifully designer-decorated modern home located in one of Sarasota's most coveted West of Trail locations - adjacent to stunning Harbor Acres! THE SPACE: This stylish, fully furnished home features three bedrooms (King, Queen, Queen), 1.5 baths, a one-car garage, a spacious, light-filled sunroom and a cozy reading nook. The home has all-new furnishings and is fully turnkey equipped to ensure a comfortable and enjoyable stay. Guests will also enjoy indoor-outdoor living with a charming front porch, al fresco dining on the beautiful back deck, and a large, well-maintained yard ideal for outdoor relaxation and entertaining. PRIME LOCATION: Located in the heart of Hudson Bayou, where you can enjoy the best of Sarasota at your doorstep! Walk to Sarasota Memorial Hospital, Marie Selby Botanical Gardens and the lively Southside Village, home to some of the city's top restaurants, bars, cafés, and shops. You're also just minutes away from Downtown Sarasota, world-famous Siesta Key Beach, Lido Key Beach, St. Armands Circle, and A-rated Southside Elementary School. PLEASE NOTE: No smoking/vaping of any kind anywhere on the property. Seasonal Rental Rates: Dec-Apr $9,000 (3 month minimum for rentals Dec - April); May-June $8,000; July-Aug $6,500, Sept-Nov - $8,000.
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