Downtown Sarasota Homes under $500,000

Downtown Sarasota Homes under $500,000

Welcome to Downtown Sarasota, a vibrant and dynamic community nestled in the heart of Sarasota County, Florida. Known for its stunning waterfront views, rich cultural scene, and charming streets, this area is a hidden gem for those looking to embrace the quintessential Florida lifestyle.

Downtown Sarasota offers an eclectic mix of dining, shopping, and entertainment options, making it a perfect place for both young professionals and families alike. Stroll down Main Street to explore unique boutiques, savor delicious cuisine at local restaurants, or enjoy a night out at one of the many theaters or art galleries. With the beautiful beaches just a stone's throw away, residents can bask in the sun or indulge in water sports whenever they desire.

For those seeking affordable housing options in this lively area, Downtown Sarasota has a delightful selection of homes priced under $500,000. Whether you’re looking for a cozy condo with stunning views of the bay or a charming bungalow just a short walk from the bustling downtown scene, there’s something for everyone. These homes offer not only an excellent investment opportunity but also the chance to be part of a thriving community filled with warmth and character.

With its perfect blend of urban amenities and natural beauty, Downtown Sarasota is an ideal place to call home. Come explore the possibilities and discover why this enchanting area is capturing the hearts of so many. Your dream home awaits in Downtown Sarasota!

Newest Downtown Sarasota Homes under $500,000

33 S Gulfstream Avenue Unit 702, Sarasota
$399,000
1 Beds ⋅ 1 Baths ⋅ Gulfstream Towers SubDv. ⋅ 34236 Zip Code
Sweeping Bay & Marina Views from a West-Facing 7th-Floor Residence The view is the star of this west-facing 7th-floor residence at Gulfstream Towers. Expansive windows and a converted enclosed balcony capture sweeping views of Sarasota Bay and Marina Jack, filling the space with natural light and offering a front-row seat to Sarasota’s spectacular sunsets. Located directly across from Marina Jack and Bayfront Park at the edge of downtown Sarasota, this one-bedroom residence combines an exceptional high-floor position with one of the city’s most walkable locations. Step outside to Main Street restaurants and cafés, galleries, theaters, boutiques, Selby Gardens and the waterfront—or enjoy the scenery and holiday fireworks without leaving home. The residence is offered turnkey furnished and is ready to enjoy as-is or update to your own style. Either way, the most important elements are already here: western exposure, abundant light, an elevated setting and wide-open water views that can’t be recreated. Gulfstream Towers offers a large bayfront pool and sundeck, fitness center, social room and library, community kitchen, BBQ grills, shared laundry on each residential floor, and one assigned covered parking space. Just minutes from Lido Beach and St. Armands Circle, this is a wonderful opportunity to create your own downtown Sarasota retreat in a truly special setting.

33 S Gulfstream Avenue Unit 702, Sarasota
33 S Gulfstream Avenue Unit 307, Sarasota
$329,900
1 Beds ⋅ 1 Baths ⋅ Gulfstream Towers SubDv. ⋅ 34236 Zip Code
NOW IS THE TIME - waterfront condo, in the heart of downtown Sarasota for this price! This beautifully redone one bedroom in one of the city's best kept secrets - Gulfstream Towers. Directly across from Marina Jack, walk to dining, nightlife, theatre and minutes to gorgeous area beaches. Perfect Pied a Terre to enjoy all Sarasota has to offer.

33 S Gulfstream Avenue Unit 307, Sarasota
707 S Gulfstream Avenue Unit 1006, Sarasota
$500,000
1 Beds ⋅ 2 Baths ⋅ Sarasota Town Of SubDv. ⋅ 34236 Zip Code
Experience the best of downtown Sarasota living from this exceptional 10th-floor residence at Essex House, ideally located at 707 S Gulfstream Avenue between Sarasota Bay, Palm Avenue and the heart of downtown. This elevated residence offers beautiful sunrise and moon views, impressive city outlooks and a unique feature rarely found elsewhere in the building: higher ceilings exclusive to the 10th floor, creating a more open and spacious feel. Essex House is an established 11-story, 76-residence condominium community offering a desirable combination of location, amenities, security and convenience. The residence includes one assigned parking space, access to private storage and bike storage, plus a new refrigerator and range installed in 2026. Recent building improvements provide added value and include a new roof in 2021, new pool deck in 2025, replacement of the rooftop air-conditioning system serving the interior common areas and hallways in 2025, a new fire-suppression pump in 2025 and generator improvements in 2025. There are currently no assessments, based on information provided by the association. Residents enjoy a heated saltwater pool, poolside gazebo, outdoor grilling and sink area, fitness center with weight and aerobic equipment, clubroom/social room, library, craft/wood working room and remodeled lobby. Essex House also offers key-fob building entry, security cameras throughout interior and exterior common areas, regular pest and fire inspections, and on-site management and maintenance Monday through Friday. The location is one of the strongest reasons to own here. Walk to Palm Avenue restaurants, galleries and boutique shopping, Burns Court, Sarasota’s Main Street, Marina Jack and the Sarasota Bay waterfront. Marie Selby Botanical Gardens is less than approximately half a mile away, while downtown festivals, the Sarasota Farmers Market, cultural venues and waterfront events are all nearby. Enjoy an easy approximately 3-mile trip to St. Armands Circle, with convenient access across the John Ringling Causeway to Lido Key and Sarasota’s Gulf beaches. Boaters will appreciate the downtown waterfront lifestyle, including access to Marina Jack, nearby boating events and the ability to arrive by boat at O’Leary’s Tiki Bar & Grill. If you are searching for a downtown Sarasota condo with water views, higher ceilings, resort-style amenities, secure access, on-site management, assigned parking, fitness facilities, saltwater pool, Sarasota Bay access and walkability to restaurants, galleries, shopping and the waterfront, this Essex House residence delivers a distinctive combination of location, lifestyle and long-term value.

707 S Gulfstream Avenue Unit 1006, Sarasota
101 S Gulfstream Avenue Unit 12C, Sarasota
$435,000
1 Beds ⋅ 2 Baths ⋅ The 101 Condominium SubDv. ⋅ 34236 Zip Code
LUXURY DOWNTOWN LIVING AT AN EXCEPTIONAL VALUE. Perched on the 12th floor of The 101 Condominium, this updated 1-bedroom, 2-bath residence offers nearly 1,000 square feet of light-filled interiors, a spacious private terrace, and vibrant city views in one of downtown Sarasota’s most coveted locations. As Sarasota’s skyline continues to evolve with new luxury towers, Unit 12C offers a rare opportunity to enjoy an established downtown address, refined amenities, and an enviable location at an attractive price point. Overlooking historic Palm Avenue, the residence is just steps from acclaimed galleries, boutiques, restaurants, and Sarasota’s cultural scene. Inside, the open floor plan features generous living and dining spaces, an eat-in kitchen with pass-through, a spacious primary suite with ensuite bath and walk-in closet, and a second full bath for guests. Directly across the street, Sarasota Bay, the Bayfront, and Marina Jack offer waterfront dining, boating, and deep-water docking, while Main Street is just one block away for even more dining, shopping, and nightlife. The 101 has recently completed an approximately $8 million modernization, including hurricane-rated sliding doors and windows, a redesigned lobby, and extensive structural improvements. Residents enjoy a heated pool, outdoor grilling area, fitness center and yoga room, library, movie theater, social room, and on-site management and maintenance. Just minutes from Lido Key, Longboat Key, and Siesta Key, Unit 12C delivers a compelling blend of luxury, location, and lifestyle in the heart of downtown Sarasota. For added convenience, Residence 12C is available for purchase furnished, if desired.

101 S Gulfstream Avenue Unit 12C, Sarasota
2121 Wood Street Unit 113, Sarasota
$244,900
2 Beds ⋅ 2 Baths ⋅ Citywalk SubDv. ⋅ 34237 Zip Code
Completely renovated and truly move-in ready, this ground-floor 2-bedroom, 2-bath condo in gated Citywalk puts you steps from Publix, Payne Park, the Legacy trail and everything downtown Sarasota has to offer. The work here is done. The kitchen was completely renovated less than three years ago with quartz countertops, new cabinetry, new appliances, and a reverse-osmosis drinking water system. Every appliance is under three years old, including a stackable washer and dryer added within the past year. The HVAC and ROOF are both about two years old, the electrical and plumbing have been updated, and the interior was freshly painted just four months ago. There is NO CARPET anywhere in this unit. This condo also has new hurricane impact windows and sliders for peace of mind. A light-filled living area opens through sliding glass doors to a private screened lanai with a garden view. The generous ensuite bedroom features a sliding barn door and a private bath, with a second bedroom and full bath for guests. Single-story living with no stairs, assigned parking, and solid block construction. The monthly fee covers water, exterior maintenance, grounds, fitness center and the community pool. No flood insurance required. The location is the rest of the story: walk to Payne Park for tennis, trails, and the playground, hop on the Legacy Trail, and reach Main Street's restaurants and theatre district in minutes. Downtown Sarasota and the world-renowned Gulf beaches are just a short drive away.

2121 Wood Street Unit 113, Sarasota
2155 Wood Street Unit A22, Sarasota
$145,000
1 Beds ⋅ 1 Baths ⋅ Park Lane SubDv. ⋅ 34237 Zip Code
Completely updated one-bedroom, one-bathroom condo in the much sought after community of Park Lane. This home offers stylish, move-in-ready living in one of Sarasota's most convenient locations. Every detail has been thoughtfully updated, creating a home that blends modern finishes with effortless, low-maintenance living. The beautifully remodeled kitchen features quartz countertops, a glass tile backsplash, stainless steel appliances, and recessed lighting, with tile flooring throughout. The updated bathroom showcases a custom frameless glass shower enclosure, and additional improvements include new doors, new windows, and updated appliances, providing peace of mind for years to come. Conveniently located just across from Publix and minutes from Downtown Sarasota, you'll enjoy easy access to award-winning dining, shopping, theaters, Payne Park, Marina Jack, St. Armands Circle, Lido Key Beach, and the world-famous beaches of Siesta Key. The community maintains a peaceful residential atmosphere with no pets and no smoking permitted. Leasing is allowed with a minimum three-month lease, limited to two leases per year. Subleasing and commercial use are prohibited. Whether you're searching for a full-time residence, seasonal retreat, or low-maintenance Sarasota getaway, this beautifully updated condominium offers exceptional value, outstanding convenience, and true move-in-ready condition. Schedule your private showing today.

2155 Wood Street Unit A22, Sarasota
615 S Palm Avenue Unit 10, Sarasota
$320,000
1 Beds ⋅ 1 Baths ⋅ New Orleans Apts SubDv. ⋅ 34236 Zip Code
WONT LAST LONG ....LOW HOA.......ONE MONTH MIN. RENTAL.........EUROPEAN STYLE CONDO IN SARASOTA DOWNTOWN & WALKING DISTANCE TO SARASOTA BAY....NOT IN FLOOD ZONE......This second floor condo has one bedroom and one bath and the laundry room is located in common area downstairs. This magnificent getaway condo is minutes to walk by the Sarasota Bay and the fabulous restaurants and entertainment. St Armond circle and Lido beach is only minutes away for your pleasure. Please call for your private tour.

615 S Palm Avenue Unit 10, Sarasota
435 S Gulfstream Avenue Unit 206, Sarasota
$399,999
2 Beds ⋅ 2 Baths ⋅ Regent Place SubDv. ⋅ 34236 Zip Code
The Regency House is in the ideal downtown location because it feels like a neighborhood with parkland and the cities bayfront Park to the West as well as Palm Avenue's Tree lined side walked street to the East. The neighbors use the sidewalks and are friendly and active. This building is just far enough from Main Street and all the fun and cultural venues, but just far enough away that it is more peaceful when activities are going on there. Walk the farmer's market and art shows on Saturday mornings and too the Opera and Theaters in the evenings. Many excellent restaurants and entertainment venues line the downtown streets. Walk to Whole foods or Marina Jack's and O'Leary's Cabana bar restaurant less than a half block away as well as stroll the art district walk a block away on your way to Main Street. Hard to beat this location and it is surrounded by some of the most luxurious condominiums in all of downtown but at the most reasonable price level anywhere in the area. With a new resort style pool being installed this summer to replace the dated pool, it will be a relaxing place to enjoy your time or get your exercise doing laps in the extended pool. There are new sunshades and BBQ areas to enjoy as well. We have an exercise area, a party/meeting room with small kitchen for events. The lobby has three convenient entrances and a full-time concierge and manager monitoring the properties security cameras and taking care of the residence owner's requests and needs. Everyone has a nice carport with insulated roofs and some guest spots plus parking on either side of the building on Gulfstream and Palm Avenues. The property is wide and not as crowded together like others in the downtown areas. This is a roomy two bedroom, two-bathroom unit with a nice sized living and dining room as well as the sunny and bright space with opening patio doors to enjoy the morning sunrises or evening moonlight. Attractive and warm wood floors in all the living areas and bedrooms add to the comfortable feel. Bright galley kitchen is easy to prepare your meals or walk five minutes to dine downtown or the neighborhoods quaint cafes, movie theater in the Burns Court area. Hard to beat the convenience to everything including medical services and hospital at short 5 minutes' drive. Airport is less than 15 minutes to pick up your guests, and our airport is quick and easy to get to your gate if you plan to travel. Fine dining on St. Armand's Circle and prime shopping on Lido Key as well as our clean quartz sand beaches like Siesta, Lido and Longboat Keys which are rated consistently among the best in the world! How can you beat all you get at this price level and the lifestyle this condominium will give you? Come take a look and live, the Sarasota Florida Lifestyle!

435 S Gulfstream Avenue Unit 206, Sarasota
1221 N Palm Avenue Unit 202, Sarasota
$375,000
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
435 S Gulfstream Avenue Unit 605, Sarasota
$429,000
2 Beds ⋅ 2 Baths ⋅ Regency House SubDv. ⋅ 34236 Zip Code
One or more photo(s) has been virtually staged. Welcome to The Regency House and to the 'gold coast of Sarasota' directly on Sarasota Bay! Priced at the lowest price per square foot in the downtown bayfront district and beyond and just reduced AGAIN! This unit is on the sixth floor and looks over the city and Palm Avenue. This condo is ready for your rehab and waiting for your own touches! Features include a brand-new A/C system, huge great room looking out to a sliding glass-enclosed lanai facing north with a peek view of Island Park and Sarasota Bay! This has a split bedroom floor plan and both bedrooms are ensuite. The primary bedroom closet is massive and there is an inside utility closet for storage or even reconfigure into a small office. There are several different views from the windows in the many rooms because of the building's unique floor plan and design! The Regency House features a 24/7 onsite concierge attendant, a library nook, club room with kitchen, small fitness center, and a heated swimming pool that is about to be totally transformed and expanded with added grill area and covered gazebo. One covered carport space is included on rotation. The Regency House sits proudly across Tamiami Trail from the Sarasota bayfront with O'Leary's and Marina Jack Restaurants and marina and Island Park. Fabulous Selby Gardens is a short distance away as are many delightful culinary experiences and shopping up and down popular Palm Avenue. Enjoy the area arts including Florida Studio Theatre-all within seconds to minutes. Come make this huge downtown condo how you want it in a very well-run condominium complex!

435 S Gulfstream Avenue Unit 605, Sarasota
101 S Gulfstream Ave Unit 9C, Sarasota
$460,000
1 Beds ⋅ 2 Baths ⋅ The 101 Condominium SubDv. ⋅ 34236 Zip Code
This is a great longterm investment upportuniy as now there is a two year rental in plce. Welcome to The 101 Condominiums overlooking Sarasota bayfront, one of the best locations in the heart of downtown Sarasota. This beautiful unit has been completely and smartly renovated ($133000+) to become a show stopper among its contemporarie. This one bedroom 2 full baths home offers the epitome of elegance, luxury, comfort and urban living. The kitchen boasts an expansive quartz waterfall style island, beautiful cabinatory/pantry and a luxurious tile backsplash. Designer Samsung appliances include the refrigerator, range, dishwasher and a drawer microwave. There is an under the sink osmosis system for your clean drinking and cooking water.Note the ample eating spaces at the island or the close by dining rarea. The laundry room is equipped with stacked Bosch washer and dryer and additional cabinets and shelving. There is also a drybar with cabinets and a wine cooler. The spacious bedroom has a walk-in closet and double sink with a lighted mirror. There is a 30inch porcelain tiles throughout the home. All doors are shaded glass. There is also a Bosch surround sound for your music listening enhancement. The sunny balcony overlooks Palm Avenue with its art galleries, antique shops, resraurants and seosenal street music and dance and it's perfect for your morning coffee or evening glass of wine. The Whole Food market, Selby Library, Saturday's Farmer's market and the Main Street with all its shops and restaurants are just stepped away. Across the street from Island Park, you will find Marina Jacks with deep harbor docking, waterfront restaurant and nightly dancing and entertainment. The 101 condominiums multi-million dollar modernization project is ongoing. If you are looking for a one bedroom 2 bath in one of the best Sarasota downtown locations with outstanding design and renovation and high end furniture, you owe it to yourself to visit this home. the monthly association fee includs bacic cable, internet and watrer. The owner is a real estate broker.

101 S Gulfstream Ave Unit 9C, Sarasota
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