Downtown Sarasota Homes with Sidewalk Exterior Features

Downtown Sarasota Homes with Sidewalk Exterior Features

Welcome to Downtown Sarasota, a vibrant gem nestled in the heart of Florida's stunning Gulf Coast. This bustling urban enclave is not just a location; it’s a lifestyle, offering a perfect blend of culture, convenience, and community. With its picturesque streets lined with palm trees and an array of amenities, Downtown Sarasota is an ideal place for those seeking a dynamic living experience.

One of the standout features of this charming neighborhood is its commitment to walkability. Homes in Downtown Sarasota boast delightful sidewalk exterior features, inviting residents to stroll through the community. Imagine stepping outside your door and being greeted by tree-lined sidewalks, perfect for morning jogs, evening strolls, or simply enjoying the sunshine with friends. These pedestrian-friendly pathways connect you to an array of local shops, gourmet restaurants, art galleries, and parks, making it easy to immerse yourself in the vibrant culture that Sarasota has to offer.

The architectural styles of homes in Downtown Sarasota are as diverse as the community itself, ranging from modern condos to historic bungalows, ensuring that there’s something for everyone. With the stunning Sarasota Bay just a stone’s throw away, residents can easily indulge in waterfront activities, from sailing to sunset picnics.

Experience the charm of Downtown Sarasota, where every day feels like a vacation. Whether you’re looking to invest in a new home or simply explore, this captivating neighborhood promises a lifestyle that’s rich in culture, community, and coastal beauty. Discover your perfect home in Downtown Sarasota today!

Newest Downtown Sarasota Homes with Sidewalk Exterior Features

$547,500
2 Beds ⋅ 2 Baths ⋅ Cityscape At Courthouse Centre SubDv. ⋅ 34236 Zip Code
Experience a distinctive downtown lifestyle from this rare two-story penthouse residence at Cityscape at Courthouse Centre. Offering two bedrooms, two baths, secure building access, elevator service, assigned under-building parking and a thoughtfully designed multi-level floor plan, this unique residence combines the character of an urban loft with the comfort and privacy of a traditional home. Exposed ductwork adds an industrial-chic aesthetic, while the private balcony offers city views and the ideal place to enjoy your morning coffee or unwind at the end of the day. The separation between the living areas and private bedroom level creates an ideal balance for everyday living, entertaining and hosting overnight guests. Ideally positioned above Main Street, you'll find yourself immersed in the energy of downtown Sarasota, where award-winning restaurants, sidewalk cafés, artisan coffee shops, boutiques, theaters, galleries, fitness studios and everyday conveniences are all near your front door. Whether enjoying a morning walk along Sarasota Bay, an evening performance at the Sarasota Opera House, cocktails overlooking the marina, or one of the city's many art festivals and cultural events, this location places the best of Sarasota within easy reach. Bayfront Park, Marina Jack, Marie Selby Botanical Gardens, Lido Beach, and the renowned shopping and dining of St. Armands Circle are all just minutes away. Thoughtfully maintained and ready for its next chapter, the residence offers timeless potential for personalization while preserving the distinctive architectural appeal of this rarely available floor plan. The air conditioning system was replaced in 2023, providing added peace of mind, while both bedrooms feature convenient motorized window shades for enhanced comfort and privacy. Whether you're seeking a full-time residence, a seasonal escape, or an elegant lock-and-leave retreat, this penthouse delivers an exceptional combination of location, style, comfort and value in the heart of one of Florida's desirable downtown destinations. Opportunities to own a two-story penthouse in Cityscape at Courthouse Centre are few and far between. Discover the possibilities, embrace Sarasota's vibrant urban lifestyle and make this exceptional residence your own.

1990 Main Street Unit 4, Sarasota
$789,000
2 Beds ⋅ 4 Baths ⋅ Marquee En Ville SubDv. ⋅ 34236 Zip Code
VIRTUALLY STAGED. Downtown Sarasota living WITHOUT the million-dollar price tag! Welcome to this gated 4-story townhome (with private elevator) offering the perfect blend of space, privacy, and walkable city living. With over 2,200 square feet, 2 bedrooms, 3.5 baths, a first-floor office, bonus room, screened outdoor living area with an outdoor kitchen, and a private 2-car garage, this home offers a combination of features that's rarely available in downtown Sarasota. The second level is thoughtfully designed for everyday living, where the kitchen opens seamlessly to the dining and living areas. Granite countertops, stainless steel appliances, natural gas cooking, abundant cabinet space, a pantry closet, and a separate laundry room—features not often found in downtown living—combine to create a space that's both functional and inviting. Tile flooring extends throughout the home, with carpet found only on the stairways.Tile flooring extends throughout the home, with carpet found only on the stairways. Thoughtfully designed storage tucked beneath the staircases makes excellent use of the space and provides room for everything from seasonal décor to everyday essentials. Upstairs you'll find two generously sized bedroom suites, while the top floor offers a versatile bonus room with a full bath that easily functions as a media room, guest suite, fitness room, or additional living space. A dramatic spiral staircase adds architectural interest while providing access to the top-level retreat. Step outside to the screened terrace complete with an outdoor kitchen, creating a rare outdoor living space that's perfect for relaxing or entertaining in the heart of downtown Sarasota. Located in the gated community of Marquee En Ville, you'll enjoy a community pool, fitness center, and one of Sarasota's most walkable locations. Stroll to Main Street's restaurants and cafés, the Sarasota Opera House, Florida Studio Theatre, art galleries, the waterfront, Marina Jack, Selby Library, the Sarasota Farmers Market, and countless downtown events. Whether you're searching for a full-time residence, seasonal getaway, or lock-and-leave lifestyle, this exceptional townhome delivers the convenience of downtown living with the space and amenities rarely found at this price. Vacant and ready for immediate occupancy. The combination of a private 2-car garage, flexible four-level floor plan, gated community, and unbeatable downtown location makes this a rare opportunity at $789,000.

235 Cocoanut Avenue Unit 108B, Sarasota
$1,395,000
2 Beds ⋅ 2 Baths ⋅ Plat Of Sarasota SubDv. ⋅ 34236 Zip Code
Experience refined downtown living from the 15th floor of The DeMarcay, one of Sarasota's premier luxury condominium residences. Perfectly positioned in the heart of downtown, this exceptional two-bedroom, two-bath residence offers the ultimate lifestyle, placing world-class dining, boutique shopping, art galleries, theaters, the Sarasota Opera, Whole Foods, the Saturday Farmers Market and the city's vibrant cultural scene just outside your door. Just a short stroll away, Sarasota Bay, Marina Jack, Bayfront Park and O'Leary's Tiki Bar provide endless opportunities to enjoy waterfront dining, boating and spectacular Gulf Coast sunsets. Inside, the residence showcases sophisticated contemporary design with an open-concept floor plan highlighted by a stunning chef's kitchen featuring quartz countertops, a waterfall island and seamless flow into the dining and living areas. Floor-to-ceiling windows and the private terrace capture beautiful city views along with a picturesque peek of Sarasota Bay. A custom-built entertainment wall and elegant dry bar with wine refrigeration create the perfect setting for entertaining, while porcelain tile flooring, designer lighting and premium finishes elevate every space. The spacious primary suite offers a custom walk-in closet and a beautifully appointed spa-inspired bath. Residents of The DeMarcay enjoy an exceptional luxury lifestyle with concierge service, valet parking, the secure Butterfly entry system, a state-of-the-art fitness center, owner's storage and a spectacular rooftop amenity level featuring a resort-style pool, outdoor kitchen, club room and panoramic views of Sarasota's skyline and bay. This is a rare opportunity to enjoy sophisticated, maintenance-free living with the very best of downtown Sarasota just moments from your front door.

33 S Palm Avenue Unit 1503, Sarasota
$695,000
3 Beds ⋅ 4 Baths ⋅ Payne Park Village Ph Ii SubDv. ⋅ 34237 Zip Code
BEST DEAL in town!! Where modern sophistication meets the energy of downtown Sarasota, this exceptional three-story residence offers a lifestyle few homes can match. Designed with one of the community's most desirable layouts, the home features additional windows that flood the second floor with natural light, creating an atmosphere that feels bright, open, and effortlessly refined. Thoughtfully curated with designer finishes throughout, the home balances clean contemporary style with everyday comfort. At its heart, the chef's kitchen showcases sleek Quartz surfaces, premium appliances, abundant storage, and an oversized island that invites everything from casual mornings to elegant entertaining. The open-concept living spaces flow seamlessly to a private balcony, while a versatile first-floor suite with its own full bath offers the ideal space for guests, a home office, or a private retreat. Upstairs, the primary suite is a sanctuary of understated luxury, complete with a spa-inspired bath and expansive walk-in closet. Every detail has been carefully selected to create an atmosphere that is both sophisticated and welcoming. Completing the home is an oversized two-car garage featuring upgraded overhead storage on both sides serving as an exceptional convenience for organizing beach gear, bicycles, and seasonal essentials without sacrificing parking or living space. Beyond your front door, the Sarasota lifestyle truly comes to life. Just a short stroll away, Payne Park offers a lush urban oasis with scenic ponds, walking paths, tennis courts, and direct access to the Legacy Trail bringing nature, recreation, and wellness seamlessly into your everyday routine. Spend your afternoons exploring downtown's celebrated culinary and arts scene, then end the day with a sunset at Lido Key. Resort-style amenities including a sparkling pool, spa, cabana, and dog park complete this exceptional lifestyle. Rarely does a home combine exceptional design, abundant natural light, thoughtful functionality, and an unmatched downtown lifestyle so effortlessly and at such a low price! This is more than a residence, it's an invitation to experience Sarasota at its finest. Schedule your private showing TODAY before it’s gone !!

2505 Boone Court, Sarasota
$120,000
1 Beds ⋅ 1 Baths ⋅ Park Lane SubDv. ⋅ 34237 Zip Code
Charming one bedroom condominium in downtown Sarasota. Unbeatable location and price! Discover the convenience and comfort in this affordable one-bedroom, one-bath condominium near downtown Sarasota. With 639 square feet of living space, this inviting retreat offers a garden-view balcony overlooking a beautifully maintained courtyard, filling your home with natural light. Freshly painted, nice tile, new blinds and refinished cabinets with granite countertops. In an ideal location, this community provides easy access to Payne Park, downtown Sarasota and Legacy Trail, making it ideal for active lifestyles. Enjoy the amenities of Payne Park, featuring the Payne Park Tennis Center with 12 Har-Tru tennis courts, eight pickleball courts, disc golf, a skate park, picnic areas, a circus-inspired playground with a small splash area, rock climbing and other activities, an amphitheater and the popular Circus Park Café. For biking enthusiasts, the nearby Sarasota Legacy Trail offers over 23 miles of scenic, non-motorized trails connecting Venice to Sarasota. Publix is also conveniently nearby. Inside, the unit features a spacious living and dining area, a galley kitchen with a Samsung stainless refrigerator and range new in 2023 and a balcony offering serene courtyard views. This is a fantastic opportunity to add your personal touch at the lowest price for a one-bedroom unit in the community. Community features include a refreshing pool, a clubhouse with a library, one assigned parking space, onsite laundry and storage lockers. With a new roof (2023) and no flooding in recent storms, according to the owner, this property offers security and stability. Don’t miss this rare opportunity to own an affordable home in Sarasota’s prime location.

2155 Wood Street Unit A14, Sarasota
$325,000
1 Beds ⋅ 1 Baths ⋅ Gulfstream Towers SubDv. ⋅ 34236 Zip Code
Discover the ultimate downtown Sarasota lifestyle from this beautifully maintained fourth-floor condominium offering partial Sarasota Bay, Bayfront Park, and Marina Jack views. Perfectly positioned at the coveted corner of Main Street and Gulfstream Avenue, this residence places the very best of Sarasota just outside your front door. Step inside to find expansive living spaces, wood-look tile flooring throughout, abundant natural light, and a warm modern aesthetic that complements the building's timeless mid-century architecture. The spacious primary suite offers comfort and privacy, while the retro-inspired bathroom preserves the character and charm that make this residence truly unique. Enjoy spectacular sunset skies from the comfort of your living room or take a short stroll to Sarasota's vibrant waterfront, renowned restaurants, boutique shopping, theaters, art galleries, farmers market, and year-round cultural events. Whether enjoying morning walks along the bayfront or evenings dining downtown, every day feels like a vacation. This well-maintained community offers exceptional amenities including a resort-style pool and expansive sun deck, social room with kitchen and dining area, refurbished lobby and common areas, updated elevators, impact-resistant windows, and attractive brick paver decking. Ideal as a primary residence, seasonal retreat, or investment opportunity, this is a rare chance to own in one of Sarasota's most desirable downtown locations where waterfront living, walkability, and urban convenience come together seamlessly.

33 S Gulfstream Avenue Unit 404, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Bay Plaza SubDv. ⋅ 34236 Zip Code
Virtually Staged. Experience spectacular Sarasota waterfront living at 1255 N Gulfstream Ave in this 2BR, 2BA res. w/ den & 2 balconies, offering 1,872 total SF, where panoramic bay views & Gulf vistas beyond Big Pass are the undeniable centerpiece. This refined Bay Plaza condo places you at the heart of the city. Floor-to-clg glass doors in the great rm open directly to a covered balcony, perfect for entertaining & enjoying sunset skies & the vibrant energy of the marina & city skyline. The main primary suite is a standout feature, boasting its own private balcony and dramatic ceiling-to-floor glass doors that offer a secluded view of the mesmerizing bay waters and Gulf horizons beyond Big Pass. This space is thoughtfully designed to maximize natural light and showcase the stunning surroundings. Additionally, a secondary bedroom suite provides sweeping views and a beautifully updated bath, offering flexibility and privacy for guests or multi-generational living. Inside, elegant tile floors extend throughout, creating a cohesive visual flow. Substantial enhancements have been implemented, hidden fire sprinkler heads, upgraded electrical & plumbing, new ductwork, soundproof underlayment. Artful millwork draws the eye to impressive high clgs, while contemporary lighting such as LED downlights & designer fixtures, built-in media storage, & floating cabinetry & buffet w/ under-cabinet LED lighting combine style & practicality. The seller invested over $100K in Harmoni cabinetry—a luxury brand renowned for quality & design. Designer shades offer privacy & light control. The state-of-the-art kitchen features a raised clg w/ ambient lighting, quartz counters, contrasting upper & lower cabinets & SS appls., highlighted by a black SS range hood. Plus a serv. entry, a lndry space, & 2nd office area. Accessibility was a key focus in the renovation. The Owner’s suite, main living area, & kitchen are all wheelchair accessible, w/ 2'8" doorways for ease of movement, a fully accessible main closet, & an adapted primary bath. Please note: while most areas are designed for accessibility, some spaces may have limitations based on individual needs. Retreat to a spa-like primary bath w/ elegant natural stone, a floating, European-inspired vanity, complemented by a sep matching vanity w/ a 2nd sink in the wet rm. The zero-entry marble shower features dual shower heads, w/ a recessed rainfall fixt. delivering a spa-inspired experience, complemented by a built-in seat for ultimate relaxation. Both baths feature elevated clgs, and are equipped w/ a premium Schluter shower syst. A dedicated office features a built-in desk w/ Corian, a window seat & etched glass doors for privacy and natural light —an ideal space for flexible living & working. As a resident of Bay Plaza, you will enjoy premium amenities: garaged pkg for 2 cars, 24/7 valet pkg, EV charging, concierge services. & recently installed hurricane-rated sliding glass doors & windows. Unwind at the heated pool, soak in the spa, or stay active in the state-of-the-art fitness rm w/ a sauna & steam rm. Perfectly positioned in the heart of downtown Sarasota, Bay Plaza places you w/in easy reach of trendy restaurants, boutiques, & Sarasota’s vibrant cultural scene, from Whole Foods to the theatre & opera. Take in spectacular 4th of July fireworks at Marina Jack’s from your own balcony, & enjoy quick access to St. Armands Circle, Longboat Key, & the city’s stunning beaches. A detailed list of upgrades is available upon request.

1255 N Gulfstream Avenue Unit 507, Sarasota
$425,000
1 Beds ⋅ 1 Baths ⋅ Frances Carlton SubDv. ⋅ 34236 Zip Code
Virtually Staged. Own a piece of downtown Sarasota history. Set along iconic Palm Avenue, the Frances Carlton is a 1924 Mediterranean Revival landmark listed on the National Register of HISTORIC Places, placing theaters, galleries, dining, and the marina nearby, while offering a sense of character and permanence rarely found today. This intimate boutique building of just 19 residences is thoughtfully maintained, with FULLY FUNDED RESERVES, completed Structural Integrity Inspection, and amenities including a private pool, garden areas, and gated assigned parking. This FULLY REMODELED second-floor residence has never been lived in since its renovation and offers a clean, modern interpretation of the building’s historic charm. With windows on three sides, a rare feature in condominium living, the home is filled with natural light throughout the day. The layout reflects its European-influenced design, with defined spaces, arched windows, and a sense of proportion setting it apart from more conventional layouts. The bright sunroom extends the living space and overlooks the pool below, ideal as a reading room, office, or quiet retreat. The residence offers one assigned, secured parking space. This is your opportunity to own a thoughtfully updated home in one of Sarasota’s most recognizable historic buildings, in a truly walkable downtown location. Don't let this one get away!

1221 N Palm Avenue Unit 202, Sarasota
$850,000
2 Beds ⋅ 2 Baths ⋅ Bay Plaza SubDv. ⋅ 34236 Zip Code
One or more photo(s) has been virtually staged. Refined downtown living awaits at Bay Plaza, a premier address along Gulfstream Avenue and one of Sarasota's most established and distinguished buildings — designed by the celebrated architect Tim Siebert. This exceptional second-floor residence offers something increasingly rare in urban living: a genuine connection to nature and neighborhood, with tree-lined street views below and partial marina glimpses that shift beautifully with the light and seasons. Perfectly positioned, this is a home that places you at the center of Sarasota's most vibrant cultural tapestry — steps from fabulous restaurants, the iconic Opera House, art galleries, charming coffee shops, live theatre, boutique shopping, and the beloved Saturday morning Farmer's Market. Yet despite this enviable proximity, the residence itself feels like a quiet retreat, grounded and peaceful above the gentle rhythm of the street. The well-executed split floor plan creates a natural sense of privacy and balance, with thoughtfully separated bedroom suites ideal for both full-time living and hosting guests. The living and dining areas are designed for effortless entertaining and everyday comfort, while a crisp, light-filled interior aesthetic is elevated by natural light and a seamless flow leading to a private covered balcony. Impact-resistant glass throughout the residence enhances safety and peace of mind, allowing you to enjoy the natural light and views with confidence. The kitchen anchors the living space with a practical and functional layout, offering considerable storage and a wine and beverage refrigerator — a thoughtful touch for those who love to entertain. The primary suite is a peaceful sanctuary, framed by large picture windows that sit among the treetops, filling the space with natural light and a serene connection to nature and the water. A generous walk-in closet with custom built-ins provides organization and ample storage. The en-suite bath is thoughtfully appointed with wood cabinetry, dual sinks, and granite countertops, complete with a soaking tub and separate shower. Bay Plaza residents enjoy a full-service lifestyle that is second to none — including 24-hour concierge, 24/7 valet service, EV charging stations, a resort-style pool and spa, and a state-of-the-art fitness center complete with sauna and steam room. The beautifully appointed lobby — a hallmark of Siebert's vision — showcases a grand piano, a library and media room, and elegant entertaining spaces for gathering with friends and fellow residents. This is a rare opportunity to own a home that offers timeless appeal, privacy, and effortless access to everything that makes Sarasota one of Florida's most coveted destinations. One or more photos has been virtually staged.

1255 N Gulfstream Avenue Unit 205, Sarasota
$229,000
2 Beds ⋅ 2 Baths ⋅ Citywalk SubDv. ⋅ 34237 Zip Code
Best Opportunity in Downtown Sarasota- Location is Key! Rarely available 2-bedroom, 2-bath second-floor corner unit in the highly sought-after CityWalk community. This gated enclave of just 71 residences offers an unbeatable downtown location with direct private access to the Legacy Trail and the expansive 29-acre Payne Park. This light-filled condo features a thoughtfully designed split-bedroom floor plan with comfortable living spaces, generously sized bedrooms, and two full bathrooms. BRAND NEW ROOF (2025), PVC Plumbing Waste Lines (2024), New Dishwasher, New Microwave, New Disposal; HVAC and Hot Water Heater (2020). Kitchen plumbing replaced (6-months), Bathroom plumbing fixtures (2021). Enjoy the convenience of in-unit laundry and relax on your private screened lanai—perfect for morning coffee or evening unwinding after a night out in downtown Sarasota. CityWalk residents enjoy a host of amenities, including a heated pool and spa, a well-equipped fitness center, and a pet-friendly environment. Within a short walk, you’ll find the vibrant heart of downtown Sarasota, offering abundant shopping, fine dining, and a thriving arts and cultural district. You’re also just minutes from world-renowned destinations such as Siesta Key Beach, Lido Key, and St. Armands Circle, as well as cultural landmarks like Marie Selby Botanical Gardens and the Sarasota Art Museum. The exceptional value of this beautiful condominium, combined with its prime downtown location and proven rental history, makes CityWalk one of the best opportunities in Sarasota’s emerging affordable downtown housing market. Perfect as a primary residence, seasonal retreat, or investment property—this is downtown living at its best!

2121 Wood Street Unit 201, Sarasota
$3,295,000
3 Beds ⋅ 4 Baths ⋅ The Edge Sarasota SubDv. ⋅ 34236 Zip Code
Under Construction. Move in this year! Residence 7B at The Edge Sarasota captures the essence of refined urban living in the heart of downtown’s vibrant Arts District. This impeccably designed three-bedroom, three-bath corner residence spans over 3,500 square feet, with floor-to-ceiling windows that fill the home with natural light. An open-concept layout is complemented by soaring ceilings and a chef-inspired kitchen featuring Italian cabinetry, quartz countertops, and a premium Sub-Zero and Wolf appliance suite thoughtfully curated for effortless, elevated living. A private terrace extends the living space outdoors, offering a serene retreat above the city’s energy. Residents enjoy exclusive access to a collection of resort-style amenities, including a pool with cabanas, state-of-the-art fitness center, yoga studio, sauna, secure parking, and pet-friendly features throughout. With just 27 residences, The Edge Sarasota offers an intimate boutique lifestyle just moments from the city’s celebrated dining, galleries, and cultural experiences perfectly reflecting Sarasota’s artful and walkable character. Renderings are conceptual and reflect the intended design and finish standards of the community.

290 Cocoanut Avenue Unit 703, Sarasota
$899,000
2 Beds ⋅ 2 Baths ⋅ Saah Sub SubDv. ⋅ 34236 Zip Code
Experience the best of downtown Sarasota living from this beautifully renovated corner-unit condominium at 707 S. Gulfstream Avenue, ideally positioned near the bayfront, Marina Jack, Bayfront Park, Main Street, Palm Avenue, restaurants, shopping, arts, and everything downtown Sarasota has to offer. Designed for buyers seeking bayfront proximity, and easy lock-and-leave living, this move-in-ready 2-bedroom, 2-bath residence combines modern updates, everyday convenience, and peace of mind. Extensively remodeled with a fresh, sophisticated aesthetic, the condo features hurricane impact windows and doors, an open-concept layout, abundant natural light, and stylish designer finishes throughout. The oversized gourmet kitchen offers quartz countertops, premium appliances, custom cabinetry, and generous space for entertaining. The spacious primary suite includes a beautifully updated spa-inspired en-suite bath, creating a comfortable private retreat. Additional upgrades include brand-new plumbing and electrical systems. The building has also recently upgraded its generator following the 2024 storms, further adding to the value and confidence of ownership. Residents enjoy secure entry, covered parking, a resort-style pool, fitness center, and club room, all in a highly desirable downtown Sarasota location. Whether used as a full-time residence, seasonal retreat, or low-maintenance second home, this renovated Sarasota condo offers an exceptional combination of location, updates, storm protection, amenities, and lock-and-leave convenience just moments from the waterfront.

707 S Gulfstream Avenue Unit 802, Sarasota
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