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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

4,571

# of Listings

2

Avg # of Bedrooms

$485

Avg. $ / Sq.Ft.

$873,387

Med. List Price

Browse Downtown Sarasota Real Estate Listings

Under $250,000

$250,000 - $500,000

1785 Properties Found. Page 38 of 119.

Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedrooms and two bathrooms, this meticulously designed residence seamlessly blends coastal elegance with modern comfort.

Step into a sunlit living space adorned with coastal-inspired décor, complemented by the stunning bay vistas from the living room, and kitchen, and primary bedroom. The fully equipped kitchen has all the appliances you could ever need to prepare your family's favorite treats, and a breakfast bar—perfect for culinary enthusiasts and casual dining alike.

The spacious primary bedroom features bay views from the windows, a private lanai access, and an attached bathroom. The primary bathroom has a double vanity, with a walk-in shower that is tiled from floor to ceiling. The second bedroom has two twin size-beds, a TV and plenty of closet space. The second bathroom has a large vanity, with a shower/tub combo.

Relax and unwind on your private lanai as you soak in the mesmerizing sunsets over the tranquil bay waters. Gulf & Bay Club Bayside offers an array of amenities, including a resort-style pool, tennis courts, fitness center, and a fishing pier for outdoor enthusiasts.

Conveniently located near Siesta Key's world-renowned beaches, shopping, and dining, this condo provides the perfect balance of serenity and accessibility. Embrace the Siesta Key lifestyle in this meticulously crafted bayfront haven.

**Taxes and fees not included.

SARASOTA

1373 SIESTA BAYSIDE DRIVE 1373-C

2 Beds

2 Baths

1,420 Sq.Ft.

$8,100

MLS#: A4594327

Experience luxury waterfront living in this stunning 2-bedroom, 2-bathroom condo situated on the second level of Gulf & Bay Club Bayside in Siesta Key, Florida. Boasting breathtaking views of the bay, this meticulously designed residence boasts comfort. Step into a spacious living area adorned with coastal finishes and large windows that invite an abundance of natural light. The open-concept kitchen is equipped with all the appliances you need and a breakfast bar, perfect for entertaining friends and family.

Retreat to the primary bedroom with its own set of french doors leading out to the lanai, overlooking the waterfront, providing a serene escape. The second bedroom has two full-size beds and plenty of closet space for personal belongings. Both bathrooms feature contemporary design and upscale amenities, creating a spa-like atmosphere.

Gulf & Bay Club Bayside offers resort-style amenities, including a private beach, pools, tennis courts, and lush landscaping. Immerse yourself in the vibrant Siesta Key lifestyle, where the white sandy beaches and azure waters are just steps away. This waterfront condo is a perfect blend of sophistication and tranquility, providing an idyllic retreat in one of Florida's most sought-after locations.

**Taxes and fees not included.

SARASOTA

1382 SIESTA BAYSIDE DRIVE 1382-C

2 Beds

2 Baths

1,280 Sq.Ft.

$8,000

MLS#: A4596171

Welcome to this fully furnished, completely turnkey, stunning 3-bedroom, 3-bath residence, perfectly located just steps from deeded beach access on the desirable south side of Siesta Key. The expansive living room and kitchen create a bright and open space, ideal for both relaxation and entertaining. With travertine flooring throughout, the interior exudes elegance and easy upkeep. All bedrooms host their bathrooms and private balconies. Enjoy the convenience of ample parking, plus the vibrant local scene nearby—bars, restaurants, grocery stores, and shops are just minutes away, or sit out by the private community pool. Whether you’re looking for a week-long getaway or a longer-term stay, this property offers flexible rental options, from weekly to seasonal leases. Don’t miss out on the opportunity to live in a prime location, with beach access and everything Siesta Key has to offer at your doorstep! In-Season rental rates are double current price.

SARASOTA

1027 CRESCENT STREET

3 Beds

3 Baths

4,268 Sq.Ft.

$8,000

MLS#: A4639469

VACATION RENTAL: A gorgeous renovated 2 bedroom, 2 bath Villa located on Lido Key just steps to the beach! Come discover Lido South, a rare beach side treasure located at the south end of Lido Key, From the front entrance you’ll be wowed by the inviting interior. Beautifully designed, light and bright…you’ll feel right at home! A cook’s gem, the sleek kitchen with top-of-the-line appliances includes Subzero, Wolf, and Bosch which overlooks the dining and living room. An extra special feature is the lovely, enclosed lanai with its own TV seating area. The master bedroom retreat has a private bath, large walk-in closet and Smart TV for private viewing. The guest room features a very comfortable queen Murphy bed and closet with private entrance. Both bathrooms are modern, sleek, and functional. A shoji sliding barn door leads to the laundry room which holds an all-in-one washer/dryer, tankless hot water heater, and more storage space. For your added comfort this Villa incudes Wifi, carport and private BBQ grill. Lido South is a friendly, relaxed community with a large Gulf side heated pool with open deck, chaises, chairs and umbrellas, Club room and guest parking. Neighbors gather at the Sun deck at sunset for cocktails, and there is always someone to chat with at the pool. Looking to explore…World famous St. Armand's restaurants and shops and South Lido Park is just a short stroll with exercise trails, kayak launch and mangrove tunnels to explore. No pets and no smoking permitted. Jan - Mar 2026 not available.

SARASOTA

1900 BENJAMIN FRANKLIN DRIVE V-15

2 Beds

2 Baths

1,442 Sq.Ft.

$8,000

MLS#: A4621429

It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the beach or bike to Siesta Key Village and enjoy the restaurants and shopping! Walking's not your thing? Call one of Siesta Key's free rides!

SARASOTA

5640 CAPE LEYTE DRIVE

3 Beds

2 Baths

2,729 Sq.Ft.

$8,000

MLS#: A4607612

Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.

Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural light. The heart of the home, the screened-in lanai, which boasts bay views, and has ample seating for you to enjoy your morning cup of coffee to the view.

The primary bedroom suite, located on the second floor, provides a private sanctuary with sweeping bay views from the balcony and has a king-size bed, attached is the spa-like bathroom featuring a luxurious dual vanity and a walk-in shower. On the first level there are the other two bedrooms. The second bedroom has a queen-size bed, plenty of closet space and a TV. The second bathroom has a large vanity with a shower/tub combo. The third bedroom has two full-size beds, which offers ample space to kick back and relax after a long day at the beach.

Step onto the private balcony to savor panoramic vistas of the bay, where you can unwind and enjoy spectacular sunsets. Gulf and Bay Club Bayside amenities, including pools, private beach access, community grills, pickle-ball & tennis courts, and a fitness center, enhance the resort-style living experience.

This condo epitomizes coastal elegance, inviting you to indulge in the beauty of Gulf and Bay Club Bayside and the captivating bay-front lifestyle it affords.

Gulf & Bay Club Bayside offers resort-style amenities, including pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.

House Rule: No smoking. No burning candles inside of lodging. No parties. No Pets.

**Taxes and fees not included.

SARASOTA

1366 SIESTA BAYSIDE DRIVE 1366-F

3 Beds

3 Baths

1,835 Sq.Ft.

$8,000

MLS#: A4598685

DOWNTOWN SARASOTA Location! Location! Location!..MORE PICTURES TO COME...This 10th floor turnkey FURNISHED two bedroom two bathroom condo is available starting December 2025! 1350 Main amenities include heated pool and spa, fitness center, Conference room and 24 hour secure lobby. One car parking space in secure garage. Move in and enjoy the Downtown lifestyle at the beautiful 1350 Main building on the corner of Main Street and Palm Avenue. Walk to the Sarasota Bay, Selby Gardens,Whole Foods, Restaurants, Theaters, Galleries and shops. Call Today!!!

SARASOTA

1350 MAIN STREET 1007

2 Beds

2 Baths

1,165 Sq.Ft.

$8,000

MLS#: A4633437

FULLY REMODELED 4 BEDROOM GREAT FAMILY HOME. NO POOL LESS EXPENSES. NO SHORT TERM RENTAL. A MUST SEE IF YOU LIKE RANCH STYLE. ALL NEW - HVAC - ELECTRIC - WINDOWS - KITCHEN - BATHS - ROOF.
NOTHING MISSED ON THIS VERY ATTRACTIVE HOME IN CHEROKEE PARK, SOUTH SIDE SCHOOL AND THE HOSPITAL CORE.

SARASOTA

1638 SOUTH DRIVE

4 Beds

3 Baths

2,919 Sq.Ft.

$8,000

MLS#: A4656081

Downtown Sarasota Sunset Towers - Short-Term Vacation Rental

This fully furnished, turnkey 6th-floor unit boasts high-end furnishings with a thoughtfully designed, relaxed atmosphere. Enjoy stunning panoramic views of Sarasota Bay and the Ringling Bridge from the expansive patio, visible from the living room, master bedroom, and guest bedroom. King size bed in Master bedroom, queen in guest bedroom. 65" new smart TV (not pictured) in living room. Electricity (up to $150), water/sewer/trash, Wi-Fi and basic cable are included in rent. 13% sales and tourism taxes apply for any rental less than 6 months. Exit cleaning is at tenants expense. HOA application is $150 (subject to change)

Amenities include a saltwater heated pool overlooking Sarasota Bay, a sun deck with grills and outdoor dining, a fitness center, and private beach access. Best of all, it's just a short walk to all that downtown Sarasota has to offer: the Farmers Market, Marina Jacks restaurant & park, Whole Foods, library, and a variety of shopping, dining, and entertainment options. St. Armand's Circle and Lido Beach are just 2.4 miles away, easily reachable by walking, bike ride, or quick car trip.

Experience vibrant city life with easy access to nature’s beauty. One covered parking space is included. Sorry, pets are not allowed. Don't miss out on this exceptional rental opportunity!

SARASOTA

11 SUNSET DRIVE 601

2 Beds

2 Baths

1,589 Sq.Ft.

$8,000

MLS#: R4908850

Welcome to Turtle House! This stunning 3-bedroom, 2-bath home with a pool is located in the heart of Sarasota. This home has been recently updated and offers a spacious backyard for you to entertain the whole family! Located only 12 minutes from the world-famous Siesta Key Beach and another three minutes away is Siesta Key Village, which is known for its exquisite restaurants and endless activities! Upon entering, you will find an open concept floor plan with plenty of natural light. There are gorgeous vinyl wood floors that run throughout the entire home. The living room has two large leather couches and is the perfect spot to relax after a day by the pool! Adjacent is the giant chef’s kitchen that boasts gorgeous navy cabinets, with a stunning grey quartz countertop. The dining room has a darling chandelier with seating for up to six. Your spacious master suite awaits! This room has a king-size bed, a 42” Smart TV, and private access to the pool area. Attached is the spa-inspired master bath. There is a gorgeous dual vanity, a large walk-in shower, and a free-standing soaking tub that has gorgeous views of the pool and backyard! The second bedroom has a queen-size bed and offers plenty of space to kick back and unwind after a day of adventure. The second bathroom boasts a gorgeous vanity and a large shower/tub combo. The third bedroom has two full-size beds with plenty of space for your personal belongings. Time to head outside! There is a couch that can accommodate up to four comfortably, along with four chaise lounges for you to soak up that Florida sunshine! The large caged-in pool is rectangular shaped and has a gorgeous tile backsplash. In addition, there is an outdoor shower for you to rinse off before heading in/out! Through the screened door, you will find the newly and completely renovated back yard which has been professionally landscaped and includeds, a fire pit surrounded by four Adirondack chairs, a corn hole set, and a hammock for your enjoyment. Just 7 miles from the world-famous St. Armand’s Circle, which offers endless boutique shopping and dining experiences, or you can enjoy an array of artistic events in Downtown Sarasota, such as the Sarasota Opera, the Sarasota Orchestra, ballet, theatre, the infamous Ringling Art Museum, Maria Selby Botanical Gardens, and Marina Jacks for boat tours. If you love outdoor adventures, come get lost amid the labyrinth of mangrove tunnels and explore their unique ecosystem aboard a rented kayak or stand-up paddleboard in South Lido Beach Park, or hike the Northern Nature Trail. This area seamlessly combines the energy and vibe of Downtown Sarasota cosmopolitan life with a seaside paradise that you don't want to miss. One visit to this St. Armand’s and you won't want to leave. House Rule: Not Pets. No smoking. No burning candles inside of lodging. No parties. This home has high speed internet with great WiFi service throughout, making it the perfect place for your workcation! Pool heating is optional, for an additional non-refundable fee of $25 per day + taxes to be paid directly to the management company after the reservation is confirmed.

**Taxes and fees not included.

SARASOTA

2232 PINE TERRACE

3 Beds

2 Baths

1,557 Sq.Ft.

$8,000

MLS#: A4510183

Experience the perfect blend of old Florida charm and new Florida luxury in this immaculate 3-bedroom, 3-bathroom plus office home located in the highly sought-after community of Bird Key. With a prime location just minutes from St. Armands Circle, Lido Beach, and downtown Sarasota, this home offers both comfort and convenience in one of Sarasota’s most desirable neighborhoods. Whether you're starting your morning with a bike ride to breakfast, spending your afternoon on the beach, or enjoying vibrant evenings in town, Bird Key places you in the heart of it all.
The home's open floor plan is designed for flexible living and effortless entertaining. Natural light fills the space thanks to large sliding glass doors that lead to the lanai and a sparkling blue pool. The first bedroom features a private en-suite bath, a large main closet along with three additional closets, and direct access to the lanai. The second bedroom includes a built-in Murphy bed and also opens to the lanai, making it ideal for guests or a multi-purpose space. The third bedroom offers its own en-suite bathroom and is beautifully lit by three French doors that open to the outside. A dedicated office provides a quiet retreat for working from home or creative endeavors.
The updated kitchen includes a spacious island and modern appliances, perfect for hosting or daily cooking. A separate climate-controlled laundry suite off the garage adds convenience. Other highlights include impact windows and doors, a new tile roof installed in 2013, a split floor plan for added privacy, and a fenced-in yard. The beautifully landscaped backyard is centered around a majestic banyan tree, creating a peaceful and picturesque setting.
This home is not in a flood zone and remained high and dry during recent storms, offering peace of mind. Optional membership to the Bird Key Yacht Club provides access to tennis courts, a fitness room, boat slips, and waterfront dining. The property is vacant and ready for immediate move-in—don’t miss the chance to make this Bird Key retreat your new home.

Owner is open to a rental agreement with an option to buy or sale of the property as well.

SARASOTA

606 OWL WAY

3 Beds

3 Baths

3,405 Sq.Ft.

$8,000

MLS#: A4650886

Congratulations and welcome to Lido Beach Club, a private ocean- front condominium community right on he Gulf coastline. Lido Beach Club is a highly desirable community, with private ocean-front beach entry. Community amenities include a fitness center, entertainment room, club house for gatherings and special events, a library and an OCEAN-FRONT HEATED POOL. This Million-dollar property will provide your family and guests convenience, luxury and comfort. This 2-bedroom, 2- bath condo features bamboo and marble tile flooring, with beautiful ocean view from the oversized balcony. Location is minutes from St. Armand's circle, the local destination for exquisite dining, shopping, salons and spas. This opportunity is THE PERFECT FAMILY BEACH GETAWAY. Secure your Holiday Plans now! A 3-month minimum rental is required. 4-month rentals are preferred. *Property has been leased Jan 2026-March 2026. Open availability April 1st through December 31st, 2025.*

SARASOTA

1212 BENJAMIN FRANKLIN DRIVE 303

2 Beds

2 Baths

1,621 Sq.Ft.

$8,000

MLS#: O6113556

OPEN for 2026 SEASON RESERVATIONS-SARASOTA POOL HOME in CORAL COVE. Just completed newly furnished and UPDATED 3BR, 3BA waterfront pool home is ready for your arrival. RENTAL HOME Available for LEASE. Coastal Living at it's best, WEST OF THE TRAIL!! This amazing home overlooks a saltwater canal with a private dock access for fishing, kayaking and boating in the Sarasota Bay. Dive-In or float in the heated in ground pool. Move-In and enjoy the Florida indoor/outdoor lifestyle. Just completed, a spacious screened lanai with a covered patio and large sunshine area to relax. Inside the home, the great room floor plan opens up the home's living area to capture the views and sunlight throughout. All three bedroom feature queen size beds and are en-suite with full size updated bathrooms. Well equipped Eat-In kitchen. Located in Sarasota, less than four miles to the beautiful #1 rated Siesta Key beaches and village. The Coral Cove neighborhood private 2-acre park is a walk away from the home. The tree lined waterfront park features a boat ramp, day dock, excellent fishing opportunities, and scenic views. This location offers endless opportunities to explore in Sarasota during your stay: Legacy Trail for bicyclists, Marie Selby Botanical Gardens, Ringling Museum, Performing Arts theaters, and Downtown Sarasota. One month minimum stay. Monthly Rates for May through November $4500 and December through April $8000, +13% tax on stays for one to six months. No PETS/ No SMOKING. Don't miss your chance to experience this true coastal rental gem. OPEN FOR 2026 SEASON RESERVATION FOR TWO MONTH OR LONGER STAY.

SARASOTA

1718 CARIBBEAN DRIVE

3 Beds

3 Baths

2,803 Sq.Ft.

$8,000

MLS#: A4643493

#A4628842

SARASOTA

1315 SIESTA BAYSIDE DRIVE 1315B

2 Beds

2 Baths

1,645 Sq.Ft.

$8,000

MLS#: A4628842

Welcome to "The Nest On Wood" a cozy & quiet 3 bed 2 bath POOL home w/ lake views that sits just a few steps from the Legacy Trail & is just a walk or bike ride from all of Sarasota's downtown amenities. Located less than 2 miles from Main St Sarasota & just 6 miles from Lido Key & Siesta Key, this house is warm & inviting w/ plenty of space to spread out & relax. Highlights include a heated salt water pool, dedicated work space, fully fenced backyard & screened lanai w/ bbq grill & lake views.

The Nest On Wood now offers a huge 32' by 14' heated salt water pebble tec pool with a built in 7' by 7' heated spa and large sun shelf. The backyard is now totally fenced with manicured tropical landscaping and lake views from the pool and screen enclosed lanai. There is also a large turf area and a BBQ area outside.

The bedroom configuration is as follows:

Master Bedroom:
King bed
2 nighstands
open shelving
closet
en suite bathroom
mounted flat screen tv
ceiling fan

2nd Bedroom:
King bed
2 nightstands
dresser
closet
mounted flat screen tv
ceiling fan

3rd bedroom:
Twin over Twin bunk bed
Separate full size bed
1 Night stand
Open shelving
Closet

The two guest rooms share a hall bathroom

SARASOTA

3210 WOOD STREET

3 Beds

2 Baths

1,766 Sq.Ft.

$8,000

MLS#: A4564469

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