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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

4,270

# of Listings

2

Avg # of Bedrooms

$496

Avg. $ / Sq.Ft.

$879,716

Med. List Price

Browse Downtown Sarasota Real Estate Listings

All listings

$250,000 - $500,000

4270 Properties Found. Page 59 of 285.

Discover the potential of this canal-front property, perfectly positioned just steps from Siesta Key Village and minutes from the island’s world-famous beach. This rare offering presents the perfect opportunity for visionaries, builders, or investors to renovate the existing home or build your custom luxury retreat in one of Sarasota’s most desirable coastal communities. With 75 linear feet of direct canal access leading into Sarasota Bay and beyond, this property offers the ideal waterfront lifestyle right from your backyard. You will also be able to enjoy the convenience of an easy stroll to the amazing shops, restaurants, and the vibrant energy of the Village, while still savoring the privacy and tranquility of being nestled on a quiet dead-end street just off Ocean Blvd. Don't miss this rare chance to create a personalized waterfront home that will provide the foundation for a remarkable coastal living experience. A 1% RATE BUY-DOWN IS AVAILABLE TO QUALIFIED BUYERS WHO WORK WITH THE SELLER'S PREFERRED LENDER.

SARASOTA

310 AVENIDA MILANO

3 Beds

2 Baths

1,949 Sq.Ft.

$1,100,000

MLS#: A4653913

One or more photo(s) has been virtually staged. Incredible Value! Don't miss this one! Buy now and enjoy for season. Welcome to The Blue Lagoon... when you walk in it feels like new construction! A private modern coastal retreat perfectly positioned on Siesta Key’s tranquil Heron Lagoon... the ultimate vacation home or investment property. This exceptional, gated quarter-acre compound offers the rare combination of serenity, design, and functionality, ideally located between Turtle Beach and Crescent Beach, just moments from the iconic Point of Rocks. Enter through a secure electric gate framed by custom wood fencing and arrive under a majestic live oak canopy that sets the tone for the natural beauty and privacy within. Designed to maximize indoor-outdoor living, the home features two expansive screened lanais, a sparkling private pool, an extensive wood deck, lush tropical landscaping, and a private dock where you can launch a paddleboard, kayak, or canoe directly into the peaceful lagoon. The single-level custom residence offers a thoughtfully designed 3-bedroom, 2-bath layout with wide-plank wood-look tile flooring in soft white and gray tones, crisp white walls, black metal hardware, and premium wood and metal ceiling fans throughout. Soaring ceilings are clad in hand-cut cypress wood shiplap, adding both natural warmth and acoustic insulation. The gourmet kitchen is a chef’s dream, featuring high-gloss European cabinetry, quartz countertops, a striking wood-grain tile backsplash, and Café Series stainless steel appliances including a six-burner gas range with a double oven and a counter-depth French door refrigerator with filtered and instant hot water. A whole-home water filtration system ensures pure water at every tap. The spacious master suite is a true sanctuary with a double-closet hallway, soaring ceilings, and a large window and sliding glass door that open to the lanai. The spa-inspired en suite bath features floating dual white European vanities, a luxurious rainwater shower with Kohler gold fixtures, floor-to-ceiling “blue skies” tile, and organic gray cobbled stone flooring. The peaceful sound of rainfall on the metal roof at the rear of the home enhances the retreat-like experience. The guest bath offers equally sophisticated design, with iridescent honeycomb tile behind a deep soaking tub and rich gray tilework throughout.
Every detail of this home has been carefully curated to reflect the essence of the Siesta Key lifestyle, luxurious, relaxed, and deeply connected to nature. Whether you’re looking for a full-time residence or a seasonal escape, The Blue Lagoon offers a once-in-a-lifetime opportunity to own a coastal property where water views, natural beauty, and modern comforts unite in perfect harmony. In addition to being a stunning private residence, this property is also ideal for seasonal use or as a high-performing vacation rental. Similar properties on Siesta Key routinely generate over $100,000 per year in rental income, making this an excellent opportunity to enjoy the home while having it support itself or even contribute toward paying it off. Use it as a vacation retreat while earning income and always have a beautiful place to stay on Siesta Key. And if your long-term vision includes building your dream home, please inquire directly about available building plans for the lot by Island Series with Yoder Homes. Visit the link for a 3D tour, video and floor plan.
https://nextlevelmediasrq.hd.pics/8234-Midnight-Pass-Rd/idx

SARASOTA

8234 MIDNIGHT PASS ROAD

3 Beds

2 Baths

1,758 Sq.Ft.

$1,100,000

MLS#: A4654399

One or more photo(s) has been virtually staged. LIDO KEY GULF-FRONT LUXURY

Wake up to the rhythm of the waves and endless Gulf views that stretch beyond imagination. Every room of this impeccably maintained 2-bedroom, 2-bath coastal retreat captures the magic of life on the water—set high on the 4th floor of one of Lido Key’s most coveted addresses.

Flooded with natural light, this refined escape blends relaxed sophistication with modern comfort. The open-concept design flows effortlessly to a sprawling 240 sq. ft. balcony, your private front-row seat to fiery sunsets and the tranquil blues of the Gulf of America. Inside, walls of glass invite the outdoors in, creating a seamless connection to sea and sky.

Perfectly positioned directly across from Lido Beach and a leisurely stroll from the world-class dining, boutiques, and charm of St. Armands Circle, this residence defines effortless island living.

The exclusive community elevates every moment with a newly redesigned lobby, state-of-the-art fitness center, resort-style heated pool, and attentive on-site management—all designed to make ownership a breeze.

Whether you’re seeking a peaceful full-time home or a luxurious vacation hideaway, this is where sophistication meets the sea—a rare opportunity to live the Gulf-front dream on the shimmering shores of Lido Key.

SARASOTA

101 BENJAMIN FRANKLIN DRIVE 46

2 Beds

2 Baths

1,515 Sq.Ft.

$1,100,000

MLS#: A4648942

This land is a RARE BEAUTY, are you dreaming of building your home where you and your family enjoy a lifestyle uniquely created for yourselves? IMAGINE a majestic home with a standalone guest house, alluring pool and gardens privately nestled among the palm trees. This property offers 2 lots, 0.45 acres / 19,456 sf. Palm Island is a community with only 298 homes where the residents enjoy gatherings in their Elsie Blair Park area.
The main home had water intrusion from hurricane Helene which has been mitigated and could be rebuilt or torn down, consult your contractor for construction specifics.
There is a Studio Unit/guest suite 576 hsf fully equipped with a full bath, kitchenette, sliding doors out to a large 120 sf wood deck above the detached 2 car garage. This would make a fabulous art studio, home office or in-law suite. The garage is a legal non-conforming space. Studio/Garage is block.
Take a stroll only 2 blocks to Siesta Key Beach and sink your toes into the luxurious quartz sand and sparkling water. The Village is minutes away where you will find fabulous restaurants, live music, specialty shops, night life, Sunday Farmers Market, art festivals and more. Take the Siesta Trolly to tour the island and beaches. You can also enjoy fishing, boating, parasailing, kayaking, swimming and snorkeling nearby.
You are very close to downtown Sarasota, St. Armands Circle and Lido Beach are just across the Ringling Causeway Bridge. The Sarasota Airport, Asolo Repertoire Theater and Ringling Museum are all within minutes of your unique estate homesite. What a wonderful place to live and call home!
Life is good at the Beach!!!

SARASOTA

105 ISLAND CIRCLE

None Beds

None Baths

0.45 acres

$1,100,000

MLS#: A4647819

Price reduced

3 UNITS in Laurel Park! This income-producing opportunity is in the coveted Downtown Historic District of Laurel Park, Sarasota. This beautifully renovated and meticulously maintained triplex blends timeless character with proven financial performance, offering the perfect combination of lifestyle and investment potential. Currently operating as an established Airbnb with Superhost status and professional management in place, this property provides steady, verifiable income with strong year-over-year performance and the flexibility to continue as a high-yield short-term rental or transition to long-term tenants for predictable cash flow.

The triplex features three charming, fully furnished units—two front units with two bedrooms and one bathroom each, and a one-bedroom, one-bathroom rear unit. Each includes private driveways, off-street parking, patios, and either in-unit or shared laundry. Situated on an exceptional flag lot with dual frontage on both Laurel Street and Ohio Place, this property offers rare privacy, accessibility, and redevelopment potential. The lot’s size and configuration make it ideal for a future custom residence, offering one of the most desirable build opportunities within Sarasota’s downtown core.

Financially, the property has a consistent and transparent performance record, generating $111,599 in 2023, $106,893 in 2024, and a projected $103,000 in 2025. Importantly, these figures already reflect reduced occupancy, as the owners reserve the property multiple times per year for family use. Without that usage, the income potential is expected to reach or exceed $120,000 annually, offering clear upside for an investor focused on maximizing returns. With stronger marketing, repeat-guest programs, and continuous availability, this property’s income could grow substantially while remaining a largely hands-off investment.

This triplex stands out not only for its returns but also for its flexibility. Investors can enjoy immediate passive income with management and future bookings already in place, or occupy one unit and rent the others to offset ownership costs. The property’s prime location within the National Historic District of Laurel Park enhances its long-term value, offering walkable access to Sarasota’s Bayfront, Selby Gardens, Main Street dining, shopping, and the city’s renowned arts and theater venues. Laurel Park’s historic charm, walkability, and strong rental demand make it one of Sarasota’s most stable and appreciating neighborhoods for both investors and homeowners alike.

With its combination of proven rental history, turnkey condition, desirable lot, and premier downtown location, this property represents a rare opportunity to own an asset that delivers reliable income today and exceptional upside tomorrow. Whether held as a passive income generator, a personal retreat with investment benefits, or the site of a future luxury home, this triplex embodies the best of Sarasota’s lifestyle, history, and growth potential. Don’t miss your chance to own this exceptional property in one of Sarasota’s most sought-after neighborhoods—where historic character meets lasting investment value.

SARASOTA

407 OHIO PLACE

5 Beds

None Baths

2,729 Sq.Ft.

$1,100,000

MLS#: A4667604

#A4666118

SARASOTA

2222 WEBBER STREET

3 Beds

2 Baths

2,410 Sq.Ft.

$1,099,999

MLS#: A4666118

Current Model Home available , 12 month leaseback at sought ever Gracewater community in the heart of Sarasota.

SARASOTA

719 MALDIVES TRAIL

4 Beds

3 Baths

3,757 Sq.Ft.

$1,099,990

MLS#: A4659082

Welcome to Gulf & Bay, Siesta Key’s premier GATED condominium association. Located in the heart of Siesta Key, completely drenched in the riches of beach living. Your new condominium is an END UNIT. Light and Bright with outstanding storybook views of Gulf & Bay community and your new condo is all updated inside. From the kitchen, bathrooms, plantation shutters, crown molding and more. Wi-Fi thermostat keyless entry! Your new condominium will be sold turnkey furnished, nothing to do except move in. Open floor plan great for entertaining. A super beverage cooler has been installed in the kitchen. You will find pull-outs and soft close doors & drawers. Two full sized beds in the guest room, and the main suite has gulf views, double vanities for convenience. Both bathrooms have walk-in showers. This is a split plan as well. What I really want you to see are the community grounds… the condo is fabulous, and this community is spectacular!!! You can search the state of Florida... no other community can compare itself to Gulf & Bay. Plus, END UNIT condos are the best - nothing compares to having an END UNIT. Gulf & Bay has 2 pools, new fitness center just steps away from the elevator plus saunas, tennis & PICKLEBALL courts, basketball, electric car charging stations, clubhouse, indoor hot tub. Another cool item is the complex is mapped out with its own app. Owners can easily navigate in and out of the grounds with your phone. No more fobs. Guld & Bay is great for rental income. If you want rental income this condo, has it for 2026. What's excellent is if you don't want this year's rental income, we will check with the office and move your tenants elsewhere in the community, let me know! 30-day minimum 12 times a year. I know it just got better, right! Want to head to the village? Just hop on the free trolley out of the gates and head to the village for dinner and shopping. The condo is easy to show. Don’t miss seeing this community and condominium… the search is over... get here before this opportunity is gone.

SARASOTA

5770 MIDNIGHT PASS ROAD 301

2 Beds

2 Baths

1,435 Sq.Ft.

$1,099,000

MLS#: A4663854

Price Reduction! An amazing year-round residence, vacation or investment property! Don't miss this rare opportunity to own a beautifully furnished 3-bedroom, 2-bath + loft unit just steps from world-renowned Siesta Beach with dedicated beach access. Recently renovated, this turnkey residence features a bright open floor plan with wood-look tile, shiplap accents, and raised ceilings in the hallways, kitchen and dining areas, a rare update in the community. The kitchen boasts solid wood cabinetry, quartz countertops, stainless appliances, and a charming, windowed breakfast nook. Enjoy multiple dining options including a formal area, bar, and a glass-enclosed lanai, perfect for entertaining. The spacious primary suite opens to a Florida room overlooking a serene pond and wildlife, with a renovated ensuite featuring dual sinks, walk-in shower, abundant storage, and a large closet. Upstairs includes a versatile loft, two guest bedrooms, and a full bath. Relax on the inviting front porch with views of Siesta’s iconic sunrises and sunsets. Additional perks include a one-car garage, private driveway, and in-unit laundry. Located in Gulf & Bay Club Bayside, a gated community with resort-style amenities: two pools, tennis/pickleball courts, clubhouse, fitness center, sauna, fishing pier, walking paths, and BBQ areas. On-site management and a one-week rental minimum make this a standout investment property with strong income potential year-round. Season is almost here! Take advantage of immediate rental income for 2026 season with a fully booked schedule

SARASOTA

1275 SIESTA BAYSIDE DRIVE 1275

3 Beds

2 Baths

1,885 Sq.Ft.

$1,099,000

MLS#: A4636765

Nestled on a tranquil street, in the highly sought-after Roberts Point neighborhood of Siesta Key, this stunning elevated home offers the perfect blend of luxury, privacy, and coastal charm. Situated just moments from the world-renowned Siesta Beach and the vibrant Siesta Village, this beautifully maintained two-story residence offers the perfect combination of comfort, convenience, and Florida living.
The layout features spacious living and dining areas, with plantation shutter windows that fill the home with natural light and allow for a seamless connection to the outdoors. The well-appointed kitchen includes modern appliances, ample cabinetry, and a large island, making it an ideal space for cooking and entertaining.
The master suite is a private retreat, with plenty of closet space and an en-suite bathroom that offers a relaxing atmosphere. Additional bedrooms are generously sized and perfect for family or guests.
Step outside to your private, nicely landscaped backyard, an ideal setting for relaxation and entertaining. Enjoy Florida’s beautiful weather on the expansive composite deck, complete with an outdoor shower—perfect for rinsing off after a day at the beach. The lush greenery and well-maintained yard create a tranquil, private oasis.
This home’s prime location offers easy access to the best of Siesta Key—whether it's lounging on the soft sands of Siesta Beach, exploring the unique shops and restaurants in Siesta Village, or enjoying local parks and recreational activities.
This is your chance to own a slice of paradise in one of the most coveted neighborhoods on Siesta Key. Schedule your private showing today and make this beautiful home your own!

SARASOTA

4117 ROBERTS POINT CIRCLE

3 Beds

2 Baths

3,480 Sq.Ft.

$1,099,000

MLS#: A4640938

Live, Earn, or Expand—Your Sarasota Dream Awaits A rare West of the Trail gem in Southpointe Shores, this expansive 2,808 sq. ft. duplex captures the essence of Florida living—sun-drenched, private, and endlessly versatile. Perfect for investors seeking strong rental returns, homeowners dreaming of living in one side while the other pays the mortgage, or anyone with a vision to combine both residences into a single-family coastal retreat, this property delivers possibilities at every turn.

Each unit has been thoughtfully updated for comfort, privacy, and modern ease. Two private entryways, fenced backyards, and brick-paver patios create an ideal balance of connection and independence—perfect for morning coffee under the palms or evening gatherings beneath the stars. Unit 1886 offers 1,639 sq. ft. with 4 bedrooms, 3 bathrooms, a screened lanai, gas range, stainless steel appliances, luxury quartz countertops, tray ceilings, and a flexible floor plan ideal for families or long-term tenants. Unit 1884 features 1,087 sq. ft., 2 bedrooms, 2 bathrooms, a sunroom, stainless steel appliances, luxury quartz countertops, tray ceilings, and a private fenced backyard, radiating coastal warmth and effortless style. Both units include indoor laundry rooms, and hurricane-impact windows— ready for immediate living or leasing.

Outside, Southpointe Shores enchants with a quiet, tree-lined neighborhood and an optional HOA membership granting access to a private boat ramp and kayak launch, perfect for sunset cruises or weekend paddle adventures on Sarasota Bay. Just minutes away, enjoy Siesta Key’s sugary sands, Downtown Sarasota’s vibrant arts and dining scene, and the boutique charm of The Landings and Gulf Gate Village. More than a duplex, this property is a lifestyle investment where flexibility, location, and long-term value converge. Live beautifully, earn effortlessly, and own a piece of Sarasota’s coastal magic in Southpointe Shores.

SARASOTA

1884 SOUTHPOINTE DRIVE

6 Beds

None Baths

2,808 Sq.Ft.

$1,099,000

MLS#: A4667273

Price reduced

Welcome to 1849 Baywood Drive in Sarasota, Florida 34231 Situated on a .26-acre lot with an impressive 92-foot seawall, this cleared and ready-to-build property offers direct canal access to little Sarasota bay with no fixed bridges and just minutes from the Gulf of Mexico. The property is also walking distance to Siesta Key Beach, consistently ranked as America’s #1 beach, celebrated for its powdery white quartz sand and turquoise water. Whether you’re an avid boater, fisherman, or simply love being near the water, this property is your gateway to the quintessential Florida lifestyle.

Imagine stepping out of your custom-built home and cruising through the open waters of Sarasota Bay in minutes, or exploring the turquoise waters near Midnight Pass, less than ten minutes away by boat. Living on a deep-water canal offers year-round enjoyment, from sunrise paddle boarding and kayaking to evening fishing and dolphin watching right from your own backyard. Local marine life includes snook, redfish, tarpon, mangrove snapper, and even gentle manatees that frequent these calm channels.

This highly desirable area of Sarasota has county-approved residential construction, saving you time and streamlining the path to building your custom coastal retreat. Custom builders in the area are well-versed in designing elevated, contemporary, and Key West–inspired homes to complement the waterfront setting—perfect for showcasing panoramic canal views and breathtaking sunsets.

Enjoy proximity to some of Sarasota’s finest amenities. Just 15 minutes to vibrant downtown Sarasota, residents can savor world-class dining, cultural attractions, and entertainment venues like The Van Wezel Performing Arts Hall, Marie Selby Botanical Gardens, and St. Armands Circle.

From tranquil canal living to convenient access to Sarasota’s cultural and coastal attractions, 1849 Baywood Drive presents a rare opportunity to design your dream home and live the ultimate Gulf Coast lifestyle in one of Florida’s most prestigious waterfront neighborhoods.

SARASOTA

1849 BAYWOOD DRIVE

None Beds

None Baths

0.26 acres

$1,099,000

MLS#: C7509071

Vacant Land Opportunity / Buildable Lot(s) – 2nd Lot available.
Build your dream home West of the Trail in the heart of Sarasota! This vacant lot offers the perfect blend of privacy, convenience, and lifestyle—just minutes from world-famous Siesta Key Beach, consistently ranked the #1 Beach in the USA.

Property Highlights:**
Spacious vacant lot ready for your vision/ Builder available as needed**

Centrally located near Sarasota’s best amenities and Sarasota Memorial Hospital**

Quiet residential setting with easy access to major roads**

Nearby Lifestyle Perks:**

Beaches: Only a short drive to Siesta Key, Crescent Beach, and Turtle Beach**

Restaurants & Shopping: Minutes from Gulf Gate Village dining, Southside Village, and Westfield Siesta Key Mall, Walk to famous Walt's Fish Market.**

Schools: Close to Top ranked Riverview High School, Brookside Middle, and Phillippi Shores Elementary**

Recreation: Legacy Trail for biking and walking, plus nearby marinas for boating enthusiasts and many golf courses in Sarasota**

This lot is an incredible opportunity to invest in Sarasota’s booming real estate market and design a custom residence that perfectly matches your lifestyle.

SARASOTA

3960 SUNSHINE AVENUE 007607003

None Beds

None Baths

0.42 acres

$1,099,000

MLS#: A4664916

Live, Earn, or Expand—Your Sarasota Dream Awaits A rare West of the Trail gem in Southpointe Shores, this expansive 2,808 sq. ft. duplex captures the essence of Florida living—sun-drenched, private, and endlessly versatile. Perfect for investors seeking strong rental returns, homeowners dreaming of living in one side while the other pays the mortgage, or anyone with a vision to combine both residences into a single-family coastal retreat, this property delivers possibilities at every turn. Each unit has been thoughtfully updated for comfort, privacy, and modern ease. Two private entryways, fenced backyards, and brick-paver patios create an ideal balance of connection and independence—perfect for morning coffee under the palms or evening gatherings beneath the stars. Unit 1886 offers 1,639 sq. ft. with 4 bedrooms, 3 bathrooms, a screened lanai, gas range, stainless steel appliances, luxury quartz countertops, tray ceilings, and a flexible floor plan ideal for families or long-term tenants. Unit 1884 features 1,087 sq. ft., 2 bedrooms, 2 bathrooms, a sunroom, stainless steel appliances, luxury quartz countertops, tray ceilings, and a private fenced backyard, radiating coastal warmth and effortless style. Both units include indoor laundry rooms, newer roofs, and hurricane-impact windows— ready for immediate living or leasing. Outside, Southpointe Shores enchants with a quiet, tree-lined neighborhood and an optional HOA membership granting access to a private boat ramp and kayak launch, perfect for sunset cruises or weekend paddle adventures on Sarasota Bay. Just minutes away, enjoy Siesta Key’s sugary sands, Downtown Sarasota’s vibrant arts and dining scene, and the boutique charm of The Landings and Gulf Gate Village. More than a duplex, this property is a lifestyle investment where flexibility, location, and long-term value converge. Live beautifully, earn effortlessly, and own a piece of Sarasota’s coastal magic in Southpointe Shores.

SARASOTA

1884 SOUTHPOINTE DRIVE

6 Beds

5 Baths

2,808 Sq.Ft.

$1,099,000

MLS#: A4667255

Price reduced

Under Construction. Expected completion January 2026. The Selby offers beauty, functionality, and sophistication all in one. Upon entering through the grand foyer with a tray ceiling, the great room welcomes guests with its spacious design, natural light, and tray ceiling. A well-equipped kitchen overlooks the casual dining area and features an impressive center island, ample counter and cabinet space, and a walk-in pantry. The covered lanai off the great room is accessed by multi-slide doors for seamless indoor/outdoor living. Dual walk-in closets and a relaxing primary bath with a dual-sink vanity, a luxe shower, linen storage, and a private water closet create a wonderful primary bedroom. Two secondary bedrooms feature roomy closets and a shared hall bath. A third secondary bedroom offers a walk-in closet and a private bath. Additional highlights include an everyday entry, a powder room, and conveniently located laundry.

SARASOTA

2573 WATERFRONT CIRCLE

4 Beds

3 Baths

4,238 Sq.Ft.

$1,099,000

MLS#: A4669756

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