Downtown Homes with Sidewalk Exterior Features

Downtown Homes with Sidewalk Exterior Features

Welcome to the vibrant heart of Sarasota, Florida—Downtown! This dynamic area is a delightful blend of urban sophistication and coastal charm, making it one of the most sought-after places to call home. With its inviting streets lined with lush palm trees and an abundance of cultural attractions, Downtown Sarasota offers a lifestyle like no other.

Imagine strolling along the picturesque sidewalks that weave through the neighborhood, where charming boutiques, gourmet restaurants, and art galleries await your discovery. The bustling farmers' market on Saturdays is a local favorite, offering fresh produce and artisan goods, perfect for those who appreciate the flavors of the region.

When it comes to real estate, Downtown Sarasota boasts a diverse array of homes, each with its unique character and charm. One standout feature of many properties in this area is their beautiful sidewalk exterior. These homes not only enhance the neighborhood's aesthetic appeal but also encourage a sense of community, inviting residents to enjoy leisurely walks and connect with their neighbors.

Whether you're looking for a chic condo with stunning waterfront views or a cozy bungalow nestled among the vibrant streets, Downtown Sarasota has something for everyone. The combination of an active lifestyle, cultural richness, and scenic beauty makes this area a true gem in Florida.

If you're ready to explore the possibilities of calling Downtown Sarasota home, let us help you find the perfect property that fits your lifestyle. Your dream home awaits in this enchanting city!

Newest Downtown 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 2 bedrooms, 2 bathrooms, 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 perfect 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. Perfectly 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 just steps from 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 very 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 most 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
$4,600,000
3 Beds ⋅ 3 Baths ⋅ Golden Gate Point SubDv. ⋅ 34236 Zip Code
PENTHOUSE with EXPANSIVE WATER VIEWS & PRIVATE GARAGE. Newly completed, Peninsula Sarasota is ideally positioned in the coveted Golden Gate Point neighborhood, offering a peaceful residential retreat just moments from the vibrancy of downtown Sarasota. Designed by Blu Interiors, each residence showcases contemporary modern elegance with calming, sophisticated palettes, soaring ceilings, and expansive wraparound terraces that seamlessly blend indoor and outdoor living. Every element reflects a thoughtful commitment to refined luxury. State-of-the-art kitchens feature sleek European cabinetry, gas cooktops, and quartz countertops, complemented by premium Wolf and Sub-Zero appliances. Additional highlights include hardwood flooring throughout, floor-to-ceiling windows that flood the home with natural light, and a private terrace equipped with a gas grill—perfect for effortless entertaining. The spacious owner’s retreat serves as a true sanctuary, complete with a generous walk-in closet, dual vanities, a soaking tub, and an oversized walk-in shower for spa-like relaxation. Residents enjoy on-site concierge services and secure, access-controlled underground parking for two vehicles, including an EV charging station. A private foyer and dedicated elevator provide direct access to exceptional amenities such as a resort-style pool and state-of-the-art fitness center, while the elegant owner’s club room offers private wine storage for each residence. The communal rooftop terrace sets the stage for unforgettable gatherings, boasting sweeping panoramic and sunset views. Peninsula Sarasota delivers a truly elevated lifestyle within a lush, tropical setting—just minutes from Sarasota’s celebrated arts, culture, dining, and award-winning beaches. A rare opportunity to experience sophisticated coastal living. Schedule your tour today!

253 Golden Gate Point Unit 902, Sarasota
$299,000
2 Beds ⋅ 2 Baths ⋅ Mentone Court SubDv. ⋅ 34236 Zip Code
Discover exceptional value in the heart of Sarasota's vibrant Rosemary District. Offered furnished and move-in ready, this beautifully updated two-bedroom residence at Mentone Court combines modern finishes, low-maintenance living, and an unbeatable downtown location—all within an intimate community of just 16 residences. Whether you're searching for a seasonal retreat or investment opportunity, this inviting home offers an ideal blend of comfort, convenience, and city living. The thoughtfully designed open floor plan creates an airy, welcoming atmosphere where the living, dining, and kitchen areas flow effortlessly together. Luxury vinyl plank flooring extends throughout the main living spaces, complemented by fresh interior paint, abundant natural light, and a neutral palette ready for your personal style. Sliding glass doors open to a the screened lanai, creating the perfect setting for morning coffee, evening relaxation, or enjoying Sarasota's year-round sunshine. The galley-style kitchen features stainless steel appliances, solid-surface countertops, generous cabinetry, and an efficient layout that keeps you connected to the main living areas while entertaining. Both bathrooms have been tastefully renovated with clean, timeless finishes, while the spacious primary suite offers a walk-in closet and en-suite bath. A comfortable guest bedroom, interior laundry closet with washer and dryer hookups, and assigned parking complete this move-in-ready residence. Mentone Court is a charming boutique community known for its peaceful atmosphere, attractive landscaping, and exceptionally low monthly maintenance fees, which include exterior maintenance, professional management, and more—making ownership both affordable and worry-free. Perfectly positioned just blocks from Downtown Sarasota, residents enjoy one of the city's most walkable neighborhoods. Stroll to the boutiques, cafés, breweries, and acclaimed restaurants of the Rosemary District before exploring nearby Main Street, the Sarasota Farmers Market, Bay Park, Marina Jack, and Sarasota's renowned Cultural Coast, featuring theaters, museums, galleries, and live entertainment. St. Armands Circle, Lido Beach, and Siesta Key Beach are all just minutes away, offering the perfect balance of vibrant downtown living and Sarasota's celebrated coastal lifestyle. Beautifully updated, furnished, and ideally located, this residence presents an outstanding opportunity to own in one of downtown Sarasota's most desirable neighborhoods.

631 N Orange Avenue Unit 108, Sarasota
$399,000
2 Beds ⋅ 2 Baths ⋅ Broadway Promenade SubDv. ⋅ 34236 Zip Code
Location, Location, Location! Welcome to Broadway Promenade, where downtown Sarasota living meets exceptional value. This beautifully maintained first floor residence offers the perfect combination of comfort, convenience, and lifestyle in Sarasota's highly sought after Arts and Theater District. Directly across the street from the Van Wezel Performing Arts Hall and The Bay Sarasota, this is your opportunity to own in one of the city's most exciting and rapidly evolving waterfront neighborhoods. Just outside your door, The Bay Sarasota is transforming 53 acres of waterfront into a spectacular public destination featuring expansive bayfront lawns, walking trails, waterfront dining, outdoor art installations, live entertainment, family gathering spaces, fitness activities, kayaking, community events, and year round concerts. Enjoy the very best of Sarasota with downtown restaurants, boutiques, galleries, theaters, Marina Jack, and the waterfront all within walking distance. Inside, this spacious two bedroom, two bathroom residence offers an inviting open floor plan with soaring ceilings, rich dark wood flooring, large bathrooms, beautiful stone countertops, quality wood cabinetry, stainless steel appliances, and a kitchen that opens seamlessly to the living and dining areas, making it ideal for everyday living and entertaining. The oversized private courtyard patio extends your living space outdoors and creates the perfect setting for morning coffee, evening cocktails, or dining al fresco. Conveniently located within the building, this residence also includes two assigned parking spaces under the building, abundant additional owner and guest parking, and a private storage room located just down the hall, providing plenty of space for bicycles, beach gear, and seasonal items. Broadway Promenade offers an exceptional collection of resort style amenities, including 24 hour concierge service, a heated swimming pool and spa, a well equipped fitness center, separate men's and women's locker rooms with private saunas, beautifully renovated hallways, and inviting common areas that create a true sense of community. Whether you are searching for a full time residence, a seasonal retreat, or an outstanding investment opportunity, this property checks every box. The residence is currently leased to an exceptional tenant who would love to remain, offering immediate rental income for investors while still providing flexibility for future occupancy. Downtown Sarasota continues to grow, and opportunities like this are becoming increasingly rare. Offering an unbeatable location, outstanding amenities, generous living space, and exceptional value, this is one of the best opportunities available in downtown Sarasota. Schedule your private showing today and experience everything Broadway Promenade and Sarasota have to offer.

1064 N Tamiami Trail Unit 1122, Sarasota
$529,900
1 Beds ⋅ 2 Baths ⋅ The 101 Condominium SubDv. ⋅ 34236 Zip Code
Virtually Staged. Luxury Downtown Living with Bay Views and Resort Style Amenities. Welcome to this beautifully remodeled one bedroom, two-bathroom residence at The 101 Condominium, offering the perfect blend of luxury, comfort, and an unbeatable downtown Sarasota location just steps from the waterfront, dining, shopping, and cultural attractions. The bright, open floor plan features elegant crown molding, premium tile flooring, custom built ins, automated shades, and designer finishes throughout. The chef inspired kitchen boasts quartz countertops, high end appliances, and abundant cabinetry. Both bathrooms have been tastefully renovated with beautiful tile work, while the spacious bedroom offers generous walk-in closets. A newer washer and dryer, one deeded parking space, and additional guest parking complete this move in ready home. Relax on your private patio while enjoying peek a boo view of Sarasota Bay, the iconic Unconditional Surrender statue, and Bayfront Park. Ideally located on the same level as the spectacular newly renovated pool, this residence offers effortless access to the expansive resort style pool deck featuring new chaise lounges, outdoor dining areas, umbrellas, and plenty of space to relax and entertain. Residents of The 101 enjoy outstanding amenities including a state-of-the-art fitness center, yoga room, library, movie theater, elegant social room, heated swimming pool, outdoor grilling area, concierge, and maintenance services. Enjoy Sarasota's most walkable neighborhood with Marina Jack, Island Park, Gallery Row, world class dining, boutique shopping, theaters, galleries, and beautiful Gulf beaches just minutes away. For added flexibility, the residence is currently leased to an exceptional tenant who would be happy to remain, providing immediate rental income for an investor if desired. Whether you are searching for a full time residence, a stylish pied a terre, or an investment opportunity, this home offers luxury, location, and exceptional value. Beautifully remodeled, virtually staged, move in ready, and priced to sell, this is one of the best values in downtown Sarasota. Schedule your private showing today.

101 S Gulfstream Avenue Unit 4J, Sarasota
$1,499,999
2 Beds ⋅ 3 Baths ⋅ Bayso Sarasota Condo SubDv. ⋅ 34236 Zip Code
WELCOME to BAYSO Sarasota, perfectly positioned in The Quay Sarasota within Downtown Sarasota's coveted Waterfront District, one of Florida's most exciting luxury neighborhoods. As this vibrant destination continues to evolve with exceptional dining, waterfront attractions, luxury residences, and cultural experiences, ownership here offers the opportunity to be part of Sarasota's next iconic chapter. | BEAUTIFULLY curated and thoughtfully designed, this 2-bedroom + den, 3-bath residence offers 1,869 square feet of interior living complemented by a 254-square-foot private terrace. Perfectly positioned on the coveted 10th level with a desirable south-facing exposure, the home is filled with natural light while offering panoramic peek-a-boo views of Sarasota Bay by day and the sparkling lights of Downtown Sarasota by night. | EVERY detail reflects refined contemporary design. The den features York natural grasscloth wallcoverings, while the adjacent full bath showcases Cole & Son Palm Leaves wallcovering and floating shelves. Designer Thibaut wallcoverings enhance the guest bedroom and bath, complemented by floating shelves, Riva European Oak flooring in the guest bedroom and walk-in closet, and wood closet shelving. | THE chef's kitchen is appointed with Italian-crafted Italkraft cabinetry, contemporary brass hardware, polished Silestone quartz, an Island Stone matte glass mosaic backsplash, upgraded stainless-steel pull-out shelving, a Grohe gold faucet, beverage refrigerator with wine drawers, and three oversized designer glass pendants trimmed in gold. | THE great room is equally impressive with distinctive Belgian wallcoverings crafted from natural waterlilies, a dramatic sculptural European chandelier, and large-format 24" x 48" porcelain tile extending throughout the foyer, hallways, kitchen, and living areas. The primary suite offers Oak flooring, a charcoal designer accent wall, enhanced closet shelving, and a spa-inspired bath featuring Italian wallcoverings, upgraded pull-out cabinetry, and contemporary Grohe accessories. |ADDITIONAL upgrades include Hunter Douglas remote-controlled sun-filtering and room-darkening shades, Samsung Smart washer and dryer, matte glass mosaic laundry backsplash, laundry room osmosis water purification system, recessed media support boxes, dimmer switches throughout, and Fanimation ceiling fans in the bedrooms, den, and great room. | LIFE at BAYSO extends beyond the residence. The spectacular fifth-floor resort deck features a heated pool and spa, expansive sun terrace with chaise lounges, fire pit, outdoor grills, outdoor shower, lush landscaping, dog park, and dog washing station. The elegant Club Room is ideal for entertaining or enjoying resident wine tastings, card games, and community events. Additional amenities include a state-of-the-art fitness center, boardroom, private offices, 24-hour reception, and a secure building designed for effortless luxury living. | MORE than a residence, this is an invitation to experience Sarasota's premier waterfront lifestyle, where timeless design, exceptional amenities, and the energy of The Quay Sarasota come together in one extraordinary home. |PRIVATE showings available by appointment.

301 Quay Commons Unit 1009, Sarasota
$2,100,000
4 Beds ⋅ 4 Baths ⋅ Marina View SubDv. ⋅ 34236 Zip Code
Spectacular views of the Bay, Marina, and City skyline from this rarely available 4 Bedroom condominium in Downtown Sarasota. Boasting over 3000 square feet of extraordinary living space, plus a deeded boat slip, this property offers you everything desirable. This gated and secure building offers the security of elevator locked entry to the owner's 5th floor home. Enjoy the privacy of His and Her baths and spacious walk-in closet in the primary suite. Two of the additional bedrooms have built-in bookcases ideally suited for a den or office. The convenience of a spacious in-unit laundry room with abundant closet space is sure to please. All the living room windows have been replaced, providing unobstructed views and high impact safety. Both AC systems were replaced in 2024 and the building experienced a new roof in 2025. Marina View on Golden Gate Point is just minutes from fine dining, shopping, the Van Wezel performing arts hall, Sarasota-Bradenton International Airport, St. Armands Circle and the beauty of Lido Beach. Come preview this fabulous home and experience the WOW FACTOR of 180 degree water views all day long!

660 Golden Gate Point Unit 51 & 52, Sarasota
$2,450,000
3 Beds ⋅ 3 Baths ⋅ Golden Gate Point SubDv. ⋅ 34236 Zip Code
Virtually Staged. Under Construction. Welcome to SIX88 — Golden Gate Point's most distinctive address. This landmark 10-story boutique tower encompasses just 10 residences, making it one of Sarasota's most exclusive waterfront communities. Residence 201 offers sweeping west-facing bay views over the John Ringling Bridge through floor-to-ceiling impact windows and sliding glass doors, with an open floor plan that lives like a single-family home. This 3-bedroom, 3-bath residence spans 2,506 total square feet, including 2,088 square feet of living space and a spacious private terrace — the ideal setting for taking in Sarasota Bay sunsets. Inside, find Thermador panel-ready appliances, custom cabinetry, designer finishes, and spa-inspired fully tiled bathrooms. Your private oversized 2-car garage sits above flood elevation and includes storage with optional lifts for up to 4 vehicles. Resort-style amenities include a rooftop terrace with a full outdoor kitchen and 360° views, heated pool, fitness center, community lounge, twin elevators, and gated security access — all with low HOA fees. Nestled in the secluded enclave of Golden Gate Point, you're steps from downtown Sarasota's dining and shopping, with St. Armands Circle, marina access, and the Bay Runner nearby. Dock access to the bay is available on site. This pet-friendly building offers low HOA fees, six-month rental flexibility, and a quiet environment — perfect for luxury buyers seeking privacy, views, and convenience.

688 Golden Gate Point Unit 201, 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
$749,000
2 Beds ⋅ 3 Baths ⋅ Rosemary Park SubDv. ⋅ 34236 Zip Code
Experience the best of downtown Sarasota living in this exceptional luxury condominium, where sophisticated design, walkable convenience, and the vibrant energy of the Rosemary District come together in one remarkable residence. This beautifully appointed TURNKEY two-bedroom, two-and-a-half-bath home is located in an exclusive boutique building with only six private residences, offering a level of privacy rarely found in the heart of downtown. Designed with timeless elegance, the open-concept floor plan showcases soaring ceilings, real hardwood flooring throughout, designer Italian cabinetry, granite countertops, stainless steel appliances, a new refrigerator, and a built-in wine bar with beverage refrigerator. Both bedrooms feature luxurious ensuite bathrooms, while the spacious primary suite opens to a private balcony overlooking the Rosemary District and downtown skyline. Thoughtfully upgraded throughout, this residence includes custom California Closets, remote-controlled blinds, new HVAC systems installed in 2024 and 2025, and a new water heater installed in 2025, all backed by transferable warranties for added peace of mind. Residents enjoy assigned covered parking, elevator access, gated entry, and additional storage, all just moments from Sarasota's most celebrated destinations. Stroll to The Bay Park, Bayfront Marina, Whole Foods, Main Street, the Saturday Farmers Market, art galleries, award-winning restaurants, live entertainment, and the flourishing Rosemary Arts District, or spend the afternoon at Lido Key Beach, just minutes away. Offering an unmatched combination of luxury finishes, boutique living, recent high-value upgrades, and one of Sarasota's most desirable walkable locations, this exceptional residence delivers the very best of downtown Sarasota living.

433 Central Avenue, Sarasota
$249,900
2 Beds ⋅ 3 Baths ⋅ Central Park SubDv. ⋅ 34236 Zip Code
INVESTORS & DIY BUYERS — THIS IS YOUR NEXT PROJECT! Welcome to Central Park II, one of Sarasota's most beloved resort-style communities, nestled along the scenic Hudson Bayou and just minutes from downtown Sarasota, Southside Village, and Selby Gardens. Unit 224 is the largest floor plan in the community at 1,224 sq ft — 2 bedrooms, 2.5 baths — and is priced well below comparable renovated units. That gap is the opportunity: bring your contractor and your vision, and create instant equity in a location that rarely trades this affordably. This unit needs a full top-to-bottom renovation, and the price reflects that — a true blank canvas for an investor's value-add project or a buyer who wants to design a home to their exact taste. Being sold strictly AS-IS; cash or renovation financing preferred. Community amenities include a heated pool & spa, lighted tennis & pickleball courts, fitness center & clubhouse, kayak launch and day dock directly on the bayou, and resort-style grounds — plus easy access to downtown dining, Southside Village shops and cafés, and Selby Gardens. A rare chance to secure serious value in downtown Sarasota — don't miss it.

850 S Tamiami Trail Unit 224, Sarasota
$2,529,000
32 Beds ⋅ 16 Baths ⋅ James Street Park SubDv. ⋅ 34236 Zip Code
SARASOTA ~ CITY OF SARASOTA ~ ROSEMARY DISTRICT ~ DOWNTOWN LIVING AND / OR INVESTMENT, WITH UPSIDE DEVELOPMENT OPPORTUNITIES! - WE ARE SELLING 4 CONTIGUOUS PROPERTIES WITH FOUR RENTAL HOMES ON AN ESTIMATED 23K SF +/- LAND!!!! Come and explore this unique opportunity to own and operate four contiguous properties with homes within the much sought after City of Sarasota "Rosemary District". The current rent roll is estimated at $100K +/-, all the current homes (4) are rented on an annual basis. The zoning does allow for short term weekly rentals, come and set up your own short term rental compound with estimated average daily rates @ $50.00 - $100.00 +/. Want another reason to look, owner will consider "owner financing" and/or selling off less then all four homes. There are just not many opportunities in the City of Sarasota to secure rezoned lands with the ability to use the current as-is property to secure carry income while waiting for the right timing to develop. The upside development in the Rosemary Zoning District: up to 7-stories with up to 30+ units. Property is very easy to show, sign is on site! NOTE: another contiguous parcel - rental home available for discussion. NOTE: future development plans viable on request!

1555 7th Street, Sarasota
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