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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

4,251

# of Listings

2

Avg # of Bedrooms

$471

Avg. $ / Sq.Ft.

$832,568

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

4251 Properties Found. Page 241 of 284.

New on site 1 day ago

Live the Sarasota Lifestyle at CitySide Apartments!

Welcome home to CitySide Apartments, where sleek design meets vibrant city living! Perfectly located in the heart of Sarasota, CitySide puts you just steps from the city’s best dining, shopping, arts, and Gulf Coast beaches.

Our studio, one-, and two-bedroom apartments feature modern, open layouts with gourmet kitchens, granite countertops, stainless steel appliances, plank flooring, and private patios or balconies—your perfect retreat after a sunny Florida day.

Soak up resort-style living everyday with EXCLUSIVE AMENITIES - ON SITE PROPERTY AMENITIES, PICKLE BALL COURTS, INSTRUCTOR-LED FITNESS CLASSES, RESORT STYLE POOL, SHUTTLE SERVICE, CONCIERGE SERVICES, 24-HOUR SECURITY, 24-HOUR ON-SITE MAINTENANCE, OFF SITE PROPERTY PROPERTY AMENITIES, GOLF ACCESS, TENNIS ACCESS, BEACH CLUB, BOAT CLUB, KAYAKING ADVENTURES, PADDLE BOARD RENTALS.

From your front door, you’re minutes from Lido Beach, St. Armands Circle, Marina Jack, and all that downtown Sarasota offers. Whether you’re looking to relax, explore, or entertain, CitySide is your perfect home base. Discover modern luxury with a Sarasota vibe—schedule your tour today!

Pricing and availability are subject to change. Rent is based on monthly frequency.
Square footage listed is an approximate value for each unit.

Lease by 09/30/2025 to win - $150 application fee waived, 1 month free rent, 4 hour boat cruise up to 6 individuals, & a round of golf at University Par Country Club.

SARASOTA

700 COCOANUT AVENUE 331

2 Beds

2 Baths

1,107 Sq.Ft.

$2,969

MLS#: A4664689

New on site 1 day ago

Live the Sarasota Lifestyle at CitySide Apartments!

Welcome home to CitySide Apartments, where sleek design meets vibrant city living! Perfectly located in the heart of Sarasota, CitySide puts you just steps from the city’s best dining, shopping, arts, and Gulf Coast beaches.

Our studio, one-, and two-bedroom apartments feature modern, open layouts with gourmet kitchens, granite countertops, stainless steel appliances, plank flooring, and private patios or balconies—your perfect retreat after a sunny Florida day.

Soak up resort-style living everyday with EXCLUSIVE AMENITIES - ON SITE PROPERTY AMENITIES, PICKLE BALL COURTS, INSTRUCTOR-LED FITNESS CLASSES, RESORT STYLE POOL, SHUTTLE SERVICE, CONCIERGE SERVICES, 24-HOUR SECURITY, 24-HOUR ON-SITE MAINTENANCE, OFF SITE PROPERTY PROPERTY AMENITIES, GOLF ACCESS, TENNIS ACCESS, BEACH CLUB, BOAT CLUB, KAYAKING ADVENTURES, PADDLE BOARD RENTALS.

From your front door, you’re minutes from Lido Beach, St. Armands Circle, Marina Jack, and all that downtown Sarasota offers. Whether you’re looking to relax, explore, or entertain, CitySide is your perfect home base. Discover modern luxury with a Sarasota vibe—schedule your tour today!

Pricing and availability are subject to change. Rent is based on monthly frequency.
Square footage listed is an approximate value for each unit.

Lease by 09/30/2025 to win - $150 application fee waived, 1 month free rent, 4 hour boat cruise up to 6 individuals, & a round of golf at University Par Country Club.

SARASOTA

700 COCOANUT AVENUE 129

2 Beds

2 Baths

1,172 Sq.Ft.

$2,969

MLS#: A4664650

Updated 9th floor two bedroom, two bathroom condo in Regency House with serene city view. Located in the heart of downtown Sarasota and just opposite the Bayfront and Marina Jacks, the Regency House is one of the most desirable buildings in Sarasota. Walking distance to the shops, restaurants, theater and the arts. All window and sliders have been upgraded to hurricane resistant and the former lanai has been enclosed and tiled to add additional square footage to the living room/ dining room area. Newer Bosch washer/dryer has been installed for added convenience.
Amenities include 24 hour Concierge, fitness center, clubroom with kitchen and outdoor swimming pool.
AVAILABLE 10/1/2025

SARASOTA

435 S GULFSTREAM AVENUE 906

2 Beds

2 Baths

1,424 Sq.Ft.

$2,950

MLS#: A4662141

The Regency house has an excellent location between Gulfstream Ave. and Palm Ave. on a tree lined street. Gulfstream and the Regency face the beautiful Sarasota Bayfront Park and Marina Jacks/Oleary's restaurants. The Park has a excellent marina with boat rentals, charters, family park with play area, and walking paths with a nice green area with bay view park benches. Regency House building is in the prime downtown location that has a neighborhood feeling. It is a short 2.5 block walk to Main St and Palm Ave. Walk to Theaters, Opera House, Farmers Market, Art Galleries and dinning along with many very enjoyable entertainment options that are less than a 10-minute walk from the Regency. Very well-kept grounds and building!
This city view unit has many upgraded features compared with most rental units in the building. The kitchen has high quality cabinets and appliances, large sink and granite countertops. Bamboo flooring throughout except bathrooms and kitchen which have ceramic tile. There is a storage room and a large storage closet. The bedroom closets have an exceptional amount of hanging space and shoe shelving. Master bathroom has a roomy shower and bedrooms are nicely sized. The open plan and large living space feels warm and inviting. There are three large patio doors that open towards the city views. Enjoy the breezes and fresh air with attractive Bahama shutters to allow partial sun and air when used. This unit gets great sunrises and the hot summer sun in the afternoon is on the other side of the building, so you can leave the shutters open for most of the day.
The building is protected by 24-hour concierge with full grounds and parking lot cameras for your security. Concierge will open the mechanical doors, or you can with a key fob. On-site manager and maintenance person for building and grounds. There is a party/community room with kitchen, small library, gym with restroom and shower. Community Heated pool with tables and sun lounges. BBQ area off large pool patio.
Two fairly new elevators, within the last 4 years, that are quick and rarely a wait. Modest but attractive lobby and three entrances. Newer carports that are assigned to the unit, there are some guests parking spots as well. Nicely landscaped grounds and sidewalks on both sides of the building.
You will enjoy living here as I have, I recently bought a unit in the building after renting this unit for three years because the location can't be beat! Opportunity to move in quickly, if needed.

SARASOTA

435 S GULFSTREAM AVENUE 706

2 Beds

2 Baths

1,424 Sq.Ft.

$2,950

MLS#: A4663635

Available 08/01/2025 ANNUALLY OR 2026 SEASONALLY (Dec.-Apr). $4900/mo.
This gorgeous 1 bedroom 1 bathroom fully furnished unit in the exclusive Terrace building on Siesta Key beach steps away from Siesta Key Village. Enjoy a swim from the elevated pool and catch a sunset while relaxing with a drink. This first floor condo offers a very large balcony with partial beach views as well as Siesta Village and is on the same floor to access the pool area. Washer and dryer are located very conveniently to the condo. This unit includes a private parking spot, direct beach access, WIFI, cable and water are included for a long term lease. Tenant pays for electric. Seasonal rental is a two month min and includes all utilities for the guests. Currently there are two queen beds but one bed can be removed and an armoire can be added if a tenant prefers. Sorry, no pets!

SARASOTA

5400 OCEAN BOULEVARD 1-5

1 Beds

1 Baths

1,099 Sq.Ft.

$2,950

MLS#: A4628649

Available October 15th 2025 for up to one year... Off-Season Rate...2950.00... Fully Furnished with Private Fenced Yard

This single-family home is located within minutes of Siesta Key Beach. This charming 4-bedroom, 2-bath home with an attached 2-car garage is situated in Phillippi Gardens. Enjoy a walk or bike ride to Phillippi Estate Park to take advantage of nature trails, fishing piers, a playground, and the weekly farmer's market.

The home is conveniently located near shops and restaurants. A fenced yard, laundry room, rear patio, and Florida Room make this a great spot to enjoy Sarasota! The owner will consider a longer-term lease.

From January through April of 2026, the rental rate is $4,500.00/month plus tax.

SARASOTA

5738 ANTILLES DRIVE

4 Beds

2 Baths

2,382 Sq.Ft.

$2,950

MLS#: A4662529

Turnkey Villa in Palm-Aire Country Club This beautifully furnished and tastefully decorated villa is located in the desirable Palm-Aire Country Club community. The home features an updated, spacious kitchen with stainless steel appliances, granite countertops, and wood cabinetry. Designed for comfort, it offers 2 bedrooms and 2 bathrooms. The primary suite includes a king-size bed, sliding glass doors opening to the lanai, and a fully renovated bathroom with dual vanities and a walk-in shower. The guest bedroom is furnished with a queen-size bed and conveniently located near the second bath. Enjoy peaceful golf course views from the enclosed and screened lanai, perfect for relaxing or entertaining. Community amenities include a heated swimming pool, with optional seasonal memberships available at Palm-Aire Country Club offering two 18-hole golf courses, clay tennis courts, an Olympic-size pool, and a fitness center. Ideally situated just minutes from University Town Center and UTC Mall with abundant dining and shopping options, and a short drive to Downtown Sarasota, St. Armands Circle, and Lido Beach. Pets are not permitted. Tenant must pay broker $75. This villa is available September to December 2025 and May to December 2026

SARASOTA

6041 CLUBSIDE DRIVE 6041

2 Beds

2 Baths

1,968 Sq.Ft.

$2,950

MLS#: A4662344

#A4658982

SARASOTA

6476 SILVERSTAR DRIVE

4 Beds

2 Baths

2,379 Sq.Ft.

$2,950

MLS#: A4658982

Monthly rate advertised subject to length and 3+ months off season lease. October and later in season rate of $4750 and up to $7000 for December January and February. Subject to change and other terms of the lease contract. pricing inquiries. Prices are subject to change due to availability, duration of stay and months chosen.

This fully furnished 2-bedroom, 2-bathroom condo invites you to stay longer, with its meticulously decorated, contemporary design featuring touches of luxury. Recently remodeled with premium materials, it offers an open-concept kitchen and living area with plenty of space to relax.

The living area seamlessly connects to a screened balcony, creating even more open space when the electric folding zebra blinds are raised, allowing easy access through sliding doors. These blinds not only provide privacy when needed but also help create a light, airy feel when fully opened.

The kitchen is designed for style and functionality, with 42” custom European cabinets, level 4 quartz countertops, a built-in counter-depth fridge, induction cooktop, convection microwave oven (Bosh), ultra-quiet dishwasher, water filtration system, and a custom wine bar corner that doubles as a work area.

Exceptional sound insulation enhances privacy, with concrete block walls between units and an acoustic-paneled wall in the living room. Floating cabinets with a built-in fireplace bring unique charm and a cozy ambiance to the space. LED lighting throughout ensures every corner is well-lit.

Both bathrooms are fully remodeled to match the condo's distinct design, each featuring spa-like rainfall shower systems with handheld wands. The guest bathroom also includes a bidet. The master bedroom features a sturdy king-size bed, while the guest bedroom has a full-over-queen bunk bed. The in-unit laundry includes a smart and quiet washer and dryer. In addition, the community offers a refreshing 8.5-foot-deep pool.

Perfectly located just a short drive from the beach and ample shopping options, this unit sits at the rear of the complex, away from the main road, offering enhanced privacy and a lounge-like feel on your private screened balcony.

SARASOTA

5611 SUMMER SIDE LANE 46B

2 Beds

2 Baths

1,233 Sq.Ft.

$2,950

MLS#: A4628828

This is a west South Gate home , a mid-century modern re-do, vinyl flooring throughout
With an optional HOA and the South Gate Recreational Center (a pool facility with a small membership fee) This is a 2 bedroom plus bonus room which can flex as office, studio, or even convert to 3rd bedroom, glass windows and doors lead out to an spacious fenced yard , Wrap around screened-in porch provides lots of bug-free outdoor space .
top-rated Southside Elementary and Brookside Middle School**, .8 mile walk to Southside Elementary
this home is in the heart of town, just minutes from **Siesta Key Beach, Sarasota Bayfront, the Legacy Trail, and 2 miles to downtown Sarasota**. easy access to shopping, dining, , 1 mile to dining/shopping in Southside Village,

SARASOTA

2408 SUNNYSIDE STREET

2 Beds

2 Baths

12,434 Sq.Ft.

$2,950

MLS#: TB8403377

Spacious unfurnished two bedroom, two bath condo on the 5th floor of THE REGENCY HOUSE with serene city view. The Regency House is one of the most desirable locations in downtown Sarasota. Located directly opposite the Bayfront and Marina Jack's as well as walking distance to the downtown shops, restaurants, and the Theater. The second bedroom boasts a built in Murphy bed and desk so it can either be utilized as an office or den and still offer additional sleeping area. The unit's flooring is entirely tiled and a new shower enclosure has been installed in the master bath. Newer Bosch washer and dryer has been added for your convenience. The tankless hot water heater affords much more usable space in the storage area just inside the entry. The building amenities include a community pool, fitness center and clubroom with kitchen. THERE IS ALSO A BUILDING CONCIERGE WHO IS ON DUTY 24 HOURS. Available July 1

SARASOTA

435 S GULFSTREAM AVENUE 506

2 Beds

2 Baths

1,424 Sq.Ft.

$2,950

MLS#: A4651128

Immaculate 2 bedroom 2 1/2 bath condo in San Marco available for rent all year or for a minimum of three months. Spacious open floor concept. Modern kitchen with large breakfast bar, granite counters, solid wood cabinets and stainless-steel appliances. Roomy bedrooms, the master bedroom offers privacy, large his and hers closets, dual vanities, walk in shower and separate tub. The condo also offers a large covered terrace ideal for entertaining. Great location! Close to Lido Beach and St. Armand’s Circle. A must see!

SARASOTA

1188 N TAMIAMI TRAIL 403

2 Beds

2 Baths

1,900 Sq.Ft.

$2,950

MLS#: A4656937

Welcome to this beautifully renovated 2-bedroom + office villa on a desirable corner lot in the sought-after Fairway Point community. Enjoy maintenance-free living with neutral ceramic tile flooring throughout, high-impact windows and doors, and an open floor plan that feels bright and welcoming.

The stunning kitchen features solid wood cabinets with rollout shelves, granite countertops, tile backsplash, and GE Café matte white appliances (including an undercounter beverage fridge) — perfect for any home chef. The spacious living and dining areas flow seamlessly into a sunny Florida room with plenty of natural light.

The primary suite offers an oversized walk-in closet and a beautifully updated bathroom with handicap-accessible features. The secondary bedroom and office provide flexibility and privacy with convenient pocket doors.

Other highlights include indoor laundry, an oversized one-car garage with epoxy flooring and storage, and an expanded paver driveway. Included in the rent, Water, Sewer, Trash.

Located close to shopping, dining, medical facilities, SRQ Airport, and just a short golf cart ride to the optional Palm Aire Country Club, featuring golf, tennis, pickleball, fitness, and more. Downtown Sarasota and world-class beaches are also minutes away!

This villa is move-in ready and available for lease — experience the Florida lifestyle today!

SARASOTA

6916 W COUNTRY CLUB DRIVE N

3 Beds

2 Baths

2,032 Sq.Ft.

$2,950

MLS#: A4657410

One or more photo(s) has been virtually staged. Welcome to the highly sought-after Cascades of Sarasota, a premier 55+ gated community where at least one tenant must be 55 years of age or older (no occupants under 19 permitted). This beautifully maintained home features soaring ceilings and a spacious split floor plan that includes a den, dinette, formal dining room, and a large screened lanai—perfect for enjoying Florida’s indoor-outdoor lifestyle.

The primary suite offers two generous walk-in closets and an expansive en-suite bath with a soaking tub, walk-in shower, and private water closet.

Enjoy resort-style amenities at the community clubhouse, which features indoor and outdoor heated pools, a hot tub, sauna, tennis courts, pickleball, a state-of-the-art fitness center, and a vibrant social calendar with events including a performing arts club.

Cable TV, internet, and lawn care are included with the rental. Conveniently located just minutes from UTC and Sarasota-Bradenton International Airport.

Schedule your private showing today and start living the Florida lifestyle you deserve!

SARASOTA

4235 63RD TERRACE E

2 Beds

2 Baths

2,464 Sq.Ft.

$2,900

MLS#: A4660830

LIDO TOWERS!!! Highly sought after FOURTH Floor 2 bedroom 2 bath condo in Lido Towers. Secure Building with Lido Beach Access. Enjoy the Beautiful Sunsets from the Sparkling Sandy Beach Across the Street. Lido Towers features a Heated Pool and Jacuzzi, BBQ on the Patio, Sauna, Clubhouse, Laundry Room on Each Floor, Guest Parking, and a Secure, Gated Building. Kayaking available one block away. Walk to Famous St. Armand's Circle to Dine at the wonderful Restaurants or Shop in the Boutiques. Downtown Sarasota just a short drive away.

Unit 408 is available October through December 31. This is a 2 bedroom / 2 bath condo. As the Fall rolls in with cooler temps and breezy conditions, escape to paradise and book this unit! What better a place to kick off the Holidays by shopping at St. Armands Circle, enjoying the stunning beaches, and bike riding around Sarasota. So many restaurants, shops, culture, etc. to mention.

Unit 408 is open and airy with newly renovated kitchen, great gulf/pool views, beach vibes, beautiful lanai and much much more. Don’t wait, this condo will not last long”.

Unit 408
Available October 20 – December 31
$2,900.00 / month

SARASOTA

1001 BENJAMIN FRANKLIN DRIVE 408

2 Beds

2 Baths

1,224 Sq.Ft.

$2,900

MLS#: A4516111

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