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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

4,296

# of Listings

2

Avg # of Bedrooms

$496

Avg. $ / Sq.Ft.

$879,977

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

4296 Properties Found. Page 210 of 287.

Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely stroll from the vibrant Siesta Key Village (packed with shops, restaurants, and entertainment!) and a short walk to the world-famous Siesta Key Beach, consistently ranked #1 in the USA! From the moment you step inside, you'll be embraced by a cozy, comfortable atmosphere and tasteful coastal decor, instantly making you feel at home in your personal island paradise. The updated kitchen is fully equipped for making meals or entertaining, and the formal dining room offers serene views of the tropical backyard where you can dine al fresco or simply soak up the sun in this quiet, family-oriented haven. With a comfortable Queen bed in the primary, two Twin/Single beds in the second bedroom, and a versatile Daybed Sofa in the third, there's space for everyone. This is the tranquil, sun-kissed escape you've been longing for, a perfect place to create unforgettable memories – your Siesta Key adventure awaits!

SARASOTA

5216 CALLE DE COSTA RICA

3 Beds

2 Baths

1,356 Sq.Ft.

$8,500

MLS#: A4607652

BOOKED FEB/APRIL 2026. AVAILABLE JANUARY 2026. UTILITIES INCLUDED. SIESTA KEY SPECTACULAR FULL BAY/INTRACOASTAL UNOBSTRUCTED VIEWS! BOOK YOUR BEACH GETAWAY NOW! Beautifully updated throughout Turnkey "top floor" Condo in this popular community of Sunrise Cove. Located on the southern end of Siesta Key, directly across the street from Turtle Beach! Upon entering the condo, you will immediately fall in love with the bright open plan dining and extended living room, all tastefully furnished and decorated. The fully equipped kitchen has quartz counters, custom cabinets and new stainless-steel appliances. The Master Bedroom has plantation shutters and more amazing views of the bay, the Master Bathroom was also expanded to provide more space and has a walk-in shower and single vanity. Luxury Vinyl in both the bedrooms and tiled throughout the living areas. Guest bedroom with queen size bed and walk-in closet, and the guest bathroom also has a walk-in shower and single vanity. From the front balcony you will have views of the Gulf, common laundry areas are on each floor, private storage lockers and a trash chute. Plus, 1 assigned parking carport in front of the building and additional guest parking. Sunrise Cove offers many social activities and amenities, which includes a large clubhouse with kitchen, billiards 2 tennis & 4 pickleball courts, fitness rooms, game room, club house, kayak racks, fishing docks, bayside picnic area with gas grills, 2 heated pools overlooking the Bay, and the Jr. Olympic pool is on a peninsula which juts out onto the Bay. Walk across the street the Turtle Beach Access, and you are right next door to Turtles Restaurant, and only .2 miles from the fabulous Ophelia's Bayfront Restaurant. There is a Free Trolley stop directly across the street from the complex, with free rides to the famous #1 Siesta Key Beach with its crystal quartz sand, Siesta Key Village where you will find shopping and restaurants. If you enjoy the nightlife, Siesta key village is where it's at! This is the absolute perfect island getaway. Don't let this one slip away!!

SARASOTA

8911 MIDNIGHT PASS ROAD 514

2 Beds

2 Baths

1,233 Sq.Ft.

$8,500

MLS#: A4588110

#1-Rated Siesta Key Beach – Close to Sarasota Memorial & Downtown Cultural Scene***Discover the perfect blend of coastal living and city convenience! This beautifully updated Sarasota home is ideally located just minutes from Siesta Key’s world-famous beach, Sarasota Memorial Hospital, and the vibrant downtown arts district — offering easy access to dining, shopping, and entertainment.***
Property Highlights: Bright, open-concept living with abundant natural light* Modern kitchen with stainless appliances & granite countertops* Screened lanai for relaxing Florida evenings* Private fenced yard with tropical landscaping* Pet-friendly (with approval) ***Prime Sarasota Location: 10 minutes to Siesta Key – with #1 Beach in the USA* Close to Sarasota Memorial Hospital, Trader Joe’s, and Southside Village8 Easy access to Downtown Sarasota, St. Armands Circle, and cultural venues like the Van Wezel Performing Arts Hall. Come stay and you to0 will see, What's all the fuss about Sarasota!

SARASOTA

2904 HOMASASSA ROAD

3 Beds

2 Baths

1,586 Sq.Ft.

$8,500

MLS#: A4669333

AVAILABLE FOR 2026 SEASON... Look at this great location Downtown Sarasota. Walk to everything. This commercial building is 3 floors with spa lounge on 1 & 2. Top floor with private elevator is the penthouse condo. This 4 bedroom is very unique with a very open floor plan and high ceilings. The kitchen has huge workable island, wine fridge, built in oven and microwave, 6 burner gas top with grilling area. A separate full length wet bar/ coffee station with 2 dishwashers and many cabinets for storage. The open concept space of dinning and living room with a non burning fire place is very soothing. long upper and lower windows and sliders lead out to a open patio balcony off the kitchen that views the city and Shelby Library. This is a great space to grill up for all your friends. The master bedroom has a delightful walk through closet / storage that leads to a nice size master bathroom with huge walk in shower. Through out the unit all rooms have very nice lighting from windows ceilings to floor. A spiral staircase takes you to the third upper floor bedroom with a 1/2 bath and it's own rooftop patio. This unit comes with two assigned covered parking spaces and guest parking lot if needed. This is a must see unit in the heart of Downtown Sarasota. Off Season 1 month min at $6200, prime season Dec to April $8500 per month includes all utilities

SARASOTA

1345 2ND STREET C

4 Beds

2 Baths

3,400 Sq.Ft.

$8,500

MLS#: A4618267

Seasonal ONLY Seasonal rental home on the water on BIRD KEY. This comfortable and cozy 4-bedroom, 3-bathroom pool home is situated directly on a canal with no bridges to the bay, able to accommodate a 26' boat. The open floor plan is flooded with natural light and features a living room that opens directly onto a huge covered lanai. Your lanai offers comfortable seating and dining, and right thru the door you'll find a paver pool deck surrounded by a beautiful garden with chaise lounges for enjoying the some fun in the sun. The kitchen has solid wooden cabinetry, custom tile back splash, breakfast bar and stainless steel appliances. The main bedroom has a king bed, easy access to the pool, large walking closet and en suite bathroom with dual vanities and water closet. Parking is one garage space available and a spacious circular driveway. This home's prime location offers easy access to Bird Key Park, St. Armand's Circle, Lido Beach and downtown Sarasota is just over the bridge for theater, museums, and the opera. Call today for a really memorable vacation in the Florida sunshine in a very special location-BIRD KEY!

SARASOTA

638 S OWL DRIVE

4 Beds

3 Baths

3,334 Sq.Ft.

$8,500

MLS#: A4673427

Price reduced

Escape to Your Perfect Tropical Retreat!

Prepare to be captivated by this stunning waterfront home, designed to make your getaway unforgettable. Step inside and bask in an open, light-filled floor plan enhanced by double French doors and over 30 windows that invite in natural light and frame breathtaking water views. The modern, fully-equipped kitchen boasts granite countertops, stainless-steel appliances, a cozy breakfast nook, and an expansive eight-seater dining table—ideal for memorable family dinners with sunset views over the water. The oversized master suite is your personal oasis, featuring a luxurious king-sized bed, a spacious walk-in closet, and private access to the wrap-around screened porch overlooking the water. The spa-like master bathroom includes a soaking tub and walk-in shower, offering the ultimate relaxation experience. Two additional bedrooms are designed to suit all your needs. One offers a queen bed, while the other doubles as an office, complete with a queen Murphy bed for extra sleeping space. Venture upstairs to discover a spacious loft, set up as a movie room with a private balcony overlooking the bay—perfect for unwinding with more stunning views. Outside, a scenic boat dock awaits, complete with water and electricity access, ideal for kayaking or docking a small boat. And when you’re ready to explore, you’ll find Sarasota Airport just 5 minutes away, downtown Bradenton and Sarasota within 10 minutes, and pristine beaches only 20 minutes from your door. Book now and start your dream vacation in paradise!

SARASOTA

7676 WESTMORELAND DRIVE

3 Beds

2 Baths

2,574 Sq.Ft.

$8,500

MLS#: A4646230

Lido Beach condo in Lido Surf and Sand, with a large porch overlooking views north up Lido Beach. Step into this split plan two bedroom, two bathroom condo with views that are breathtaking. The condo has porcelain tile floors and stylish furniture.

SARASOTA

1102 BEN FRANKLIN DRIVE 514

2 Beds

2 Baths

1,213 Sq.Ft.

$8,250

MLS#: A4431393

Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.

As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are evident in every detail, from the soothing color palette to the carefully selected furnishings that create a sense of laid-back elegance.

The spacious kitchen is a chef's delight, featuring all the appliances you need, and ample cabinet space. Whether you're preparing a quick breakfast or hosting a family dinner party, this kitchen is as functional as it is stylish.

The living room seamlessly flows into a private balcony, where views of the bay and the boat slip invite you to unwind and enjoy the gentle sea breeze. Imagine sipping your morning coffee or toasting to spectacular sunsets as you watch boats gently navigate the waters.

The two bedrooms provide peaceful sanctuaries. The primary bedroom boasts an attached bathroom, complete with two vanities and a walk-in shower. The second bedroom is perfect for family and friends, and has plenty of room to unwind after a day at the beach. The second bathroom is adjacent and has an updated vanity with a shower/tub combo.

Gulf & Bay Club Bayside offers an array of amenities! Guests can also enjoy the community pool, tennis courts, and well-maintained grounds, enhancing the overall coastal living experience.

Siesta Key's famous white sand beaches are just moments away, providing endless opportunities for relaxation and recreation. Indulge in the vibrant local culture, with eclectic shops, delicious dining options, and a lively arts scene.

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

**Taxes and fees not included.

SARASOTA

1343 SIESTA BAYSIDE DRIVE 1343-C

2 Beds

2 Baths

1,280 Sq.Ft.

$8,200

MLS#: A4593764

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

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

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

#A4664965

SARASOTA

6722 ROXBURY DRIVE

3 Beds

2 Baths

2,958 Sq.Ft.

$8,000

MLS#: A4664965

Seasonal/short term Live at the beach downtown Sarasota with amazing views of Sarasota Bay! This fully and beautifully renovated 2/2 unit is filled with natural light from floor to ceiling new impact windows with custom electric shades. The flooring is all solid surface -LVP and marble so no carpeting! The kitchen is spacious with solid wooden cabinetry topped with slab granite counters with waterfall side and breakfast bar, custom subway tile design backsplash, pantry and complimented with stainless steel appliances. The living room and dining room are open planned with your view of the bay. The bedrooms are roomy and the master has an organized walk in closet and en suite bathroom. There is a washer and dryer in unit for your convenience. This community has it's own private beach, a large saltwater heated pool, fitness center, kayak storage and water access. This unit is super convenient to shopping, fine and casual dining, theater, library, opera, museums and Lido Beach, just over the bridge. This property can be rented during high season (Dec thru April) at $8000/month + tax with 3 month minimum or off season (rest of the year) at $6000/month + tax. Call today for your dream vacation home!

SARASOTA

11 SUNSET DRIVE 704

2 Beds

2 Baths

1,603 Sq.Ft.

$8,000

MLS#: A4653789

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

3rd floor beautifully appointed. 2 bedroom 2 bath Unit is available Seasonal $7500; Yearly or 6 month rental $4500.000 Underground parking (1) space. Your own private washer and dryer inside unit. Tennis and pickle ball courts. Private Beach with Chairs. 2 heated pools, fitness room, clubhouses, fishing pier. Location is great.

SARASOTA

1200 E PEPPERTREE LANE 305

2 Beds

2 Baths

1,400 Sq.Ft.

$8,000

MLS#: A4649129

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