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Downtown Sarasota

One of the most popular communities provided by Michael Graf

Downtown Sarasota

About Downtown Sarasota

Living in downtown Sarasota, Florida offers a vibrant blend of urban sophistication and coastal charm. This lively neighborhood is known for its stunning bayfront views, cultural attractions, and a diverse array of dining and shopping options. Residents enjoy easy access to world-class art galleries, theaters, and festivals that showcase the area’s rich artistic heritage. The nearby sandy beaches provide a perfect escape for sun-seekers and outdoor enthusiasts, while the city's parks and waterfront promenades promote an active, healthy lifestyle. With a strong sense of community and a dynamic atmosphere, downtown Sarasota is not just a place to live; it’s a lifestyle that embraces both relaxation and excitement.

One of the most popular communities provided by Michael Graf

3,927

# of Listings

2

Avg # of Bedrooms

$488

Avg. $ / Sq.Ft.

$877,505

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

3927 Properties Found. Page 199 of 262.

RENTED JAN., FEB., MARCH., 2026. This 2nd floor Carlton featuring 2 bedrooms and 2 baths and offers one of the most spectacular views from the screened and glass-enclosed lanai of the lake and golf course that you will find in the entire community. Nicely furnished with a king bed in the master, twins in guest, flat-screen TVs, internet access, very well equipped kitchen, you will want for nothing, one car detached garage, heated pool and tennis courts right outside your door; golf membership transfers for $250 if desired. Stoneybrook is a gated community with impressive clubhouse featuring one of Sarasota's finest restaurants, plus fitness center, several heated pools, and an 18 hole par 72 premier golf course recently refurbished, and har-tru tennis courts also refurbished. All this and minutes from world-famous Siesta Key sugar sandy beaches, shops & restaurants. CALL FOR OFF-SEASON RATES

SARASOTA

8911 VERANDA WAY 222

2 Beds

2 Baths

1,555 Sq.Ft.

$5,000

MLS#: A3984795

Turnkey Seasonal Rental in Sarasota Harbor East, fabulous bay views from every window, 2 bedrooms, two baths, updated and tile floors throughout. Lovely four season Lanai overlooking Sarasota Bay, watch the Dolphin and Manatee while you sip your morning coffee. The community offers a lovely heated pool, clubhouse, grills, kayak storage and boat slips on a first come, first served basis. Walk to all the shops and restaurants on St. Armands Key, spend the day at beautiful Lido Beach or stroll over the bridge to Downtown Sarasota. You will love this great community and location. This is a 55+ community. Booked end of January thrught the endo of March, 2024.

SARASOTA

769 JOHN RINGLING BOULEVARD 36EXET

2 Beds

2 Baths

1,042 Sq.Ft.

$5,000

MLS#: A4586107

#A4544030

SARASOTA

4705 HOLLINGSWORTH AVENUE

3 Beds

2 Baths

1,350 Sq.Ft.

$5,000

MLS#: A4544030

JUST LISTED! 2026 SEASONAL RENTAL - 2 bed/2 bath upstairs condo w/elevator! This well appointed condo is within a 5 minute drive to the world famous Siesta Beach ...yet it is on the mainland! The complex has a nice community heated pool and is VERY close to restaurants and shopping, It's a 10 minute drive to downtown Sarasota where you can enjoy the Opera, Library, farmers market,gourmet shops and MORE. The condo is available NOVEMBER 1ST ( @4,000) DEC @4,000. January, FEB, MARCH @5,000.00 EACH. ( 3 MONTH MINIMUM) + taxes and a one time exit cleaning fee of $200.00. This is a NON SMOKING CAMPUS. A small dog may be accepted. Don't be left in the coldd!!

SARASOTA

3360 S OSPREY AVENUE 210B

2 Beds

2 Baths

1,122 Sq.Ft.

$5,000

MLS#: A4643488

AVAILABLE NOW, GROUND FLOOR VERANDA ON THE GOLF COURSE is bright and cheerful and tastefully decorated and sure to delight, 2 bedroom, 2 bath with front and rear lanai space - rear lanai is glassed and screened providing extra living space - and there is a one-car garage. King bed in the master bedroom with an adjoining updated bathroom with walk-in shower, queen bed in 2nd bedroom adjacent to a full bathroom. Kitchen with eating space, pantry, quartz countertops, and newer cabinets, is separated from the dining area with a breakfast bar. There is tile in the main living area and carpets in the bedrooms. There is no membership offered with this residence; however, you can dine at the clubhouse and the Fairway Veranda's heated pool is right across from the condo. The complex borders the Legacy walking and biking trail access, is less than 15 minutes from Siesta Key beaches, the village shops and restaurants. You can be downtown Sarasota in 25 minutes to enjoy the culinary and cultural flavors that Sarasota offers. This is a vacation condo that will not disappoint.

SARASOTA

9641 CASTLE POINT DRIVE 1215

2 Beds

2 Baths

1,555 Sq.Ft.

$5,000

MLS#: A4664283

Pet-friendly, SARASOTA FURNISHED, Phillippi Creek area east of Tamiami Trail. 1 month minimum rental.
Rented January 11, 2026 - March 7, 2026.
This 3 bedroom + den pool home with high ceilings and open concept floor plan lends itself to family gatherings and entertaining. You will love the modern kitchen with granite island and counters and oversized ceramic tile throughout. Inside Laundry room and 2 car garage. Entertain with the Weber BBQ grill on the pool deck and relax by the solar heated pool surrounded by your PRIVATE, FENCED BACKYARD. The Master Bedroom has 2 closets and a dual sink bathroom with walk-in shower. This fabulous south Sarasota location is just minutes to Siesta Key beaches, great shopping, Phillippi Creek Estate & Outdoor Farmhouse Market every Wednesday, nearby waterfront dining & more.
Rental includes pool maintenance, lawn care and streaming channels including YOUTUBETV and Netflix. Tenant responsible for electric and water bill, WI-FI.

SARASOTA

2330 BRADFORD STREET

3 Beds

2 Baths

1,884 Sq.Ft.

$5,000

MLS#: A4477491

AVAILABLE OFF-SEASON ONLY. This third-floor vacation condo with absolutely one of the best views in Stoneybrook. Two bedrooms, two baths, king bed in master, queen in the guest bedroom, internet access, flat-screen TVs and a NEW KITCHEN complete with granite countertops. Eating space in kitchen, living room/dining room combo, one covered parking space. ALL NEW FLOORING throughout, everything you need for a few months in the sunshine. Golf membership transfers for a fee if desired (check with clubhouse for cost) and the heated pool and tennis courts are right across from the building. Members can dine at the impressive clubhouse, use the fitness center, enjoy the Arthur Hills designed premier golf course, lounge at the pool, play tennis, and enjoy the many activities the club has to offer. Stoneybrook is a gated community conveniently located on Palmer Ranch, giving quick access to shopping, banks, restaurants, I-75, and less than 15 minutes to the sugary sandy beaches of Siesta Key. The Legacy Walking and Biking Trail access is just a block from the entrance to the community and it's a short drive to downtown Sarasota.

SARASOTA

9300 CLUBSIDE CIRCLE 1307

2 Beds

2 Baths

1,314 Sq.Ft.

$5,000

MLS#: A4481790

New on site 1 day ago

AVAILABLE SHORT TERM or LONG TERM. Discover the charm of this 3 bedroom, 2 bathroom home with ceramic tile flooring throughout and a laundry room with clothes washer and dryer. 3039 Chase Circle is nestled in the heart of Gulf Gate in Sarasota, Florida just 2.4 Miles to the BEACH. This inviting cheerful residence offers a sunny, harmonious blend of comfort and convenience, making it an ideal choice for those seeking a vibrant yet tranquil living experience. Two car attached garage. Property has washer and dryer. Situated in the Gulf Gate Estates neighborhood, residents appreciate the area's dog-friendly atmosphere, well-maintained yards with mature palm trees and gardens, and easy access to grocery stores and restaurants and the #1 rated best beach Siesta Key Beach. Just minutes away, you'll find the world-renowned Siesta Key Beach, celebrated for its pristine sands and clear waters. For shopping and dining enthusiasts, St. Armands Circle offers a variety of boutiques and eateries. Nature lovers can explore the nearby Myakka River State Park, perfect for hiking and wildlife observation. Embrace the opportunity for 3039 Chase Circle, where the best of Sarasota's amenities are within your reach.

SARASOTA

3039 CHASE CIRCLE

3 Beds

2 Baths

2,329 Sq.Ft.

$5,000

MLS#: A4669035

Available May 1, 2026 for an annual lease! Rarely available 3 bed, 3 bath, plus office/work-space condo in sought-after Somerset Cay! You will love the resort-style amenities and the contemporary elegance this wonderful home offers. There are three balconies, offering views of the Bay, the Intercoastal Waterway and the Gulf. Fully updated kitchen with top-of-the-line appliances and breakfast bar, a large primary suite with a King bed, with access to the private balcony. The spacious primary bath offers dual sinks, a soaking tub and walk-in shower. Both guest bedrooms are elegantly appointed, you will appreciate the tasteful decor and original artwork! This boutique-style community offers a heated pool and spa, well-equipped fitness center, cabanas, BBQ area and kayak launch, to name a few. Located on the south end of the Key, you are just down the street from popular Turtle Beach, and many dining and shopping options, both on the Key and off. Welcome to your slice of Paradise!

SARASOTA

9122 MIDNIGHT PASS ROAD 34

3 Beds

3 Baths

3,010 Sq.Ft.

$5,000

MLS#: A4581541

New on site 1 day ago

AVAILABLE DEC. 2025, JAN., FEB., MARCH, APRIL 2026 and off-season. VACATION IN STYLE IN THIS 3-BEDROOM GROUND FLOOR TOTALLY UPDATED UNIT AT PINESTONE. Quartz countertops in kitchen, new cabinets, new appliances, all new furniture throughout, smart TVs, new carpet in the living room and bedrooms, and a new washer and dryer. Lots of natural light lend to the bright and cheerful atmosphere in this well-furnished and tastefully decorated condo. The glassed and newly screened lanai gives that added year-round space, and they have added new outside patio space. They have thought of everything. This is the perfect vacation condo decorated in a coastal theme, offering everything you would need for a few months in the sunshine. Pinestone is an amenity-rich community featuring a huge heated pool, a 32-seat movie theater, a gathering room, a fitness center, a billiards room, a card room, two lighted tennis/pickleball courts, a firepit area, and much more. The Legacy trail access is a short distance from the community and it is less than 15 minutes to the sugar sandy beaches of Siesta Key. You can be downtown Sarasota in less than 25 minutes to enjoy the many restaurants, performing arts, the Ringling Museum of Arts, and many more cultural experiences.

SARASOTA

8369 WINGATE DRIVE 2114

3 Beds

2 Baths

1,405 Sq.Ft.

$5,000

MLS#: A4669140

DOWNTOWN SARASOTA...!ANNUAL UNFURNISHED WATERFRONT CONDO AVAILABLE IN ONE WATERGATE. Stunning views abound from this 1736 Sq. Ft 2 Bedroom, 2 Bath Condo in the heart of downtown Sarasota. The condo features a large wraparound balcony, impact resistant windows, large closets with organizers, and a spacious kitchen with granite countertops. There is also an additional in-unit storage room with cabinets and an additional refrigerator. One Watergate amenities include a heated saltwater pool, grilling area, two roof top tennis courts, and social room. One garage space is included. Laundry is located just outside the unit. Water, cable/internet are included. Walk to the waterfront, restaurants, shopping and theaters. All within minutes away. A short drive to beautiful LIDO BEACH. CALL NOW FOR A SHOWING BEFORE IT'S GONE!

SARASOTA

1111 N GULFSTREAM AVENUE 16C

2 Beds

2 Baths

1,996 Sq.Ft.

$5,000

MLS#: A4650116

#A4543933

SARASOTA

4705 HOLLINGSWORTH AVENUE Lower

3 Beds

2 Baths

1,236 Sq.Ft.

$5,000

MLS#: A4543933

RENTED, DEC 2025 JAN THROUGH APRIL 2026: GROUND FLOOR END UNIT at Stoneybrook Terraces, spacious vacation rental with golf course view, bright and cheerful, designer decorated, new carpet, new furnishings, new paint, new appliances, immaculate and offering all you will need for a few months in the sunshine. Golf membership transfers to the tenant if desired. The Terraces has tennis courts and the all-popular pickleball plus heated pool and is the closest community to the impressive clubhouse where you will find a fitness center, large heated pool, and, of course, the newly modernized 18-hole Kipp Schultes premier designed golf course, impeccably maintained, Har-Tru lighted tennis courts and all the activities you would expect from a country club. Stoneybrook is a gated community located on Palmer Ranch just minutes from Siesta Key beaches, shops, and restaurants. The Legacy walking and biking trail is two blocks from the entrance, the YMCA, Publix, CVS, Walgreens, and several banks are nearby.

SARASOTA

8735 OLDE HICKORY AVENUE 8101

2 Beds

2 Baths

1,449 Sq.Ft.

$5,000

MLS#: A4489419

Looking for the ultimate Siesta Key getaway? This stunning 3-bedroom, 2-bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to the lively Siesta Key Village! Available Nov 1-Dec 21, 2025, and May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the moment you step inside. The open and inviting great room is perfect for gathering with friends and family, whether you’re relaxing after a day in the sun or entertaining guests. The spacious kitchen, with a cozy dining area off to the side, makes it easy to enjoy meals together. Plus, a laundry room and 2-car garage ensure convenience throughout your stay. Step outside and discover your own private oasis – a large screened lanai featuring an in-ground heated pool, perfect for swimming or lounging under the sun. Whether you prefer soaking up rays or unwinding in the shade, the lanai offers ample space for everyone to enjoy. The privacy-fenced backyard adds a secluded feel, making it the perfect spot to relax in peace. With electric, internet, basic cable, pool service, and grounds maintenance included, all you have to worry about is enjoying your time in paradise. Reach out today to secure your seasonal stay in this desirable Siesta Key retreat! Monthly rates are $5000 May through October, November $5750, December $6750, January through April $8500. 13% tourism tax must be added to all leases 6 months or less. 30 Day minimum term. Sorry, NO ANNUAL leases available, and no pets permitted.

SARASOTA

735 BIRDSONG LANE

3 Beds

2 Baths

2,784 Sq.Ft.

$5,000

MLS#: A4660352

Kingston Arms on St. Armands Circle turn-key furnished Condo, 2 beds, 2 baths, second floor overlooking a quiet residential street. Look no further for the perfect vacation retreat. No need for a car, walkable to the many fine shops and local restaurants, take the BayRunner Trolley to downtown Sarasota for the day, book a guided Kayak tour through the mangrove tunnels or spend the day at Lido Beach, only a four minute walk! Many dates available and rates vary by season.

SARASOTA

500 S WASHINGTON DRIVE 5B

2 Beds

2 Baths

1,102 Sq.Ft.

$5,000

MLS#: A4604124

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