Mid Town Sarasota Homes with Booker High High School

Sarasota Pool Home with NO HOA and Major Recent Updates! A screened pool, a spacious fenced backyard, no HOA, and several major recent improvements make this three-bedroom Sarasota home an especially appealing find. Inside, the home features a comfortable living area with crown molding, tile and laminate wood flooring, and a bright kitchen with quartz counters, white cabinetry, stainless steel appliances, recessed lighting, generous counter space, and a large island/breakfast bar. The screened swimming pool offers plenty of surrounding deck space for relaxing, dining, and entertaining. Beyond the pool enclosure, the expansive fenced backyard provides even more room for pets, gardening, recreation, or creating your own outdoor retreat. Several important improvements have already been completed, including a new A/C system in 2025, water main and backflow system in 2026, and roof in 2019. The refrigerator and dryer were also replaced in 2026. An attached one-car garage provides additional storage and everyday convenience. Conveniently located near Downtown Sarasota, the home offers easy access to shopping, dining, entertainment, parks, and the area’s many cultural attractions. Whether you are purchasing your first home, downsizing, or simply looking for a Sarasota pool home without HOA restrictions, this property offers comfort, convenience, and plenty of room to enjoy the Florida lifestyle.

3338 Bailey Street, Mid Town Sarasota

$999,000

5 Beds ⋅ 4 Baths ⋅ A4703278 MLS

Three renovated units, one corner parcel, four blocks from Main Street. A fully occupied Sarasota triplex producing $7,200 per month, or $86,400 annually, against a $999,000 asking price. That is an 8.65% gross yield and a basis of $333,000 per door. Every unit has been rebuilt inside. Large-format marble-look porcelain tile runs wall to wall through all three, with no carpet anywhere in the building. Walls and ceilings are crisp white under flush-mount LED fixtures in every room. Kitchens carry light flat-panel cabinetry, and stainless appliances, with stacked laundry inside the unit rather than a shared machine down the hall. Bathrooms are white vanities, chrome fittings and framed mirrors over the same tile. The finish package is deliberately consistent across all three units, and that consistency is what makes it turnkey: one material palette, one maintenance standard, and no unit sitting in line for work before it can lease. The mix spans three price points. A three-bedroom, two-bath at $3,800. A two-bedroom, one-bath at $1,900. A studio at $1,500. All three are occupied. The building is single-story concrete block on a slab under a shingle roof, with central air, public water and public sewer, and off-street parking for ten. Three water meters and three electric meters measure consumption per unit. The parcel sits in Flood Zone X. Between masonry construction and Flood Zone X, the two variables that drive Florida insurance both point the same direction. Ownership is fee simple with no HOA, no condominium association and no CDD fee. Two levers sit on top of the in-place rent. The first is vacation rental. The City of Sarasota extended its vacation rental ordinance to the Downtown Neighborhood zone district in March 2024, and this parcel falls inside it. Stays of seven nights or longer are permitted with a city certificate, which is a materially different revenue profile than a twelve-month lease in a location four blocks off Main Street. The second is the land. A 12,472 square foot corner site, zoned DTN and sitting under the City's Missing Middle Overlay, which can support density beyond the three units standing today where attainable-housing, design and permitting standards are satisfied. Nothing further is approved and any concept requires confirmation with the City, but the parcel carries a second thesis that a stabilized triplex elsewhere does not. Renovated, occupied, individually metered, insurable, and sitting on urban ground with room to grow. Income now, optionality later.

431 N East Avenue, Mid Town Sarasota

$1,250,000

3 Beds ⋅ 4 Baths ⋅ A4703244 MLS ⋅ Premier On Main BLDG.

SPACIOUS 2,762 sq ft, LIGHT-FILLED END UNIT with significant recent upgrades, an attached 2-car garage plus additional carport at Premier on Main offers comfort, quality, and all the buzzing life of Downtown in the Uptown area. Sarasota without the bustle. Flexible floor plan allows for guests, roommates, and work-from-anywhere convenience with the ease of lock-and-leave living. FEATURES: Contemporary architecture & styling, Modern color palette and superior finishes, 3 ensuite bedrooms & baths, 3.5 baths, His and Her Master Custom California Closets, Private elevator, Lockout first floor suite, 4181 Sq ft total space, 620 sq ft deck spaces, 9ft ceilings, Japandi-style wet room in primary suite, KitchenAid appliances, large island, bar-height counter + custom pantry. Rooftop deck ready for your outdoor kitchen and entertainment amenities, Turnkey, pristine condition. PREMIER PERKS: LOW HOA $446/mth(landscape, water, sewer, trash), Flood Zone X, Weekly, monthly rentals, long-term leases allowed. Pet friendly |Energy efficient systems, Impact-rated windows & doors, Security system, Whole home water filtration, On-demand gas water heater. SARASOTA LIFE ELEVATED: Year-round sunshine, outdoor living, and a walkable culture bring the best of Florida to life. This urban-convenient location is bike-friendly with direct access to the Legacy Trail or hop on the nearby Bay Runner trolley for complimentary rides through downtown to Lido Beach and St Armands Circle. Take morning runs over the John Ringling Bridge, or kayak in the bay. Stroll through Main Street’s arts and cultural district, bike to the farmer’s market or Bayfront Park. Explore the lively restaurant and music scene to find your new favorite hang outs. End your days with drinks on the rooftop, enjoying the solitude or surrounded by family & friends, above the city lights and beneath the stars.

72 N School Avenue, Mid Town Sarasota

$145,000

2 Beds ⋅ 3 Baths ⋅ A4703066 MLS ⋅ 3365 BLDG.

Virtually Staged. Step into affordable Florida living in Ramblewood Acres! This condo is situated in a well estbablished gated community known for its convenience to all the best places in Sarasota. This well maintained, move-in-ready townhome offers a smart, functional layout. Granite counters, stainless steel appliances, and a passthrough to the dining area - perfect for easy entertaining. The large living area offers a main-level half bath for extra convenience. Upstairs, two large bedrooms each feature private en-suite baths and oversized wall to wall closets. One bedroom offers a serene balcony and the other a generous sundeck, your choice of personal retreat. Ramblewood Acres offers three pools, including one heated pool, a dog park, clubhouse, basketball and tennis courts, playground, and shuffleboard. New Roof, Fresh Interior Paint, New Tile Flooring in the front patio! Fees include basic cable, pest control, on-site management, and more for low-maintenance living. The location puts you nearby everything. Charming downtown Sarasota, Baltimore Orioles Baseball, St. Armands Circle for shopping and dining, escape to any one of our beautiful beaches including nearby world famous Siesta Key or Lido beach. Stunning sunsets, Powder Sand, and Crytal Blue waters! UTC’s shopping and dining are within a short drive, and SRQ Airport is conveniently nearby. Golfers will love the convenience of having the newly renovated Bobby Jones Golf Course just around the corner or the Meadows Golf Club now open to the Public. Well-funded association reserves help support the community’s long-term maintenance and capital improvement needs. Don’t miss this opportunity, schedule your showing and discover your Florida lifestyle right here on the Suncoast!

3365 Ramblewood Drive N Unit 35C8, Mid Town Sarasota

$349,900

2 Beds ⋅ 1 Baths ⋅ A4700512 MLS

Sweet Downtown Sarasota Cottage with Timeless Southern Charm - Charming, inviting, and full of character, this delightful 2-bedroom, 1-bath cottage captures the essence of old-Florida living in the heart of Downtown Sarasota. Framed by a classic picket fence and welcoming front porch, this is the kind of home that immediately feels special. Picture yourself relaxing with a glass of sweet tea on the porch, enjoying the easy pace of cottage living, then strolling to some of Sarasota’s wonderful restaurants, shops, galleries, and cultural destinations just beyond your doorstep. Inside, timeless details and thoughtful improvements create a warm and comfortable atmosphere. Beautiful hardwood floors grace the main living spaces, while built-in kitchen features add the character and charm that are increasingly hard to find in today’s homes. With 8-foot ceilings and an inviting layout, the home offers an appealing blend of vintage personality and everyday functionality. Numerous updates provide peace of mind, including new windows (2021), new refrigerator (2019), new washer and dryer (2019), new ceiling fans (2019), added insulation (2019), and new vinyl fencing (2019), roof is few years old and electric totally updated. Whether you’re searching for a charming primary residence, a Sarasota getaway, or an income-producing property, this cottage offers exceptional versatility. Located within Sarasota’s Downtown Neighborhood (DTN) district, the property is surrounded by the energy and convenience of downtown while retaining the intimate feel of a true neighborhood. There is no HOA and no CDD fee, and the property is located in the X flood zone, meaning flood insurance is not required by the lender based on the information provided. Enjoy downtown dining, shopping, art, entertainment, and cultural attractions virtually at your doorstep, with convenient access to bus routes and the beautiful Gulf beaches.

2048 5th Street, Mid Town Sarasota

$239,900

2 Beds ⋅ 2 Baths ⋅ A4702073 MLS ⋅ 12 BLDG.

Experience the best of Sarasota living in this beautifully maintained first-floor residence in the sought-after gated Villagio community. This spacious split-bedroom floor plan offers the perfect blend of comfort, privacy, and convenience, featuring an open living area, generous primary suite with walk-in closet, and a private covered lanai ideal for enjoying Florida’s year-round sunshine. Villagio offers resort-style amenities including a heated pool, fitness center, clubhouse, tennis and pickleball courts, putting green, and beautifully maintained grounds. Ideally located just minutes from Downtown Sarasota, St. Armands Circle, Lido Key, Siesta Key, SRQ Airport, and Ed Smith Stadium—the spring training home of the Baltimore Orioles—this home places the very best of Sarasota right at your doorstep. Perfect as a primary residence, seasonal retreat, or investment opportunity.

1010 Villagio Circle Unit 104, Mid Town Sarasota

$490,000

3 Beds ⋅ 2 Baths ⋅ A4701774 MLS

Welcome to this charming 3-bedrooms, 2-bathrooms single-family home located in the heart of downtown Sarasota. House with 2 beds/1bath front of house. Rear side of house 1 unit with 1Bed/1bath apartment/mother-in-law. ZONING DOWNTOWN NEIGHBORHOOD This spacious home features a newly renovated kitchen, new flooring and a large backyard perfect for entertaining. Walking distance to nearby downtown restaurants, shopping, entertainment, wholefoods, Marina Jacks, the Van Wezel Performing Arts Center, Selby Library, Ringling Bridge and a short hop over to St. Armand’s Circle, Lido and Longboat Key. Don’t miss out on this amazing opportunity to own a piece of paradise in Beautiful Sarasota Downtown!! Call now to schedule your private showing!!

2031 4th Street, Mid Town Sarasota

$439,900

4 Beds ⋅ 2 Baths ⋅ A4699486 MLS

------MOTIVATED SELLER********HOME HAS GREAT POTENTIAL. ORIGINAL 4 BEDROOMS, 2 BATHS, A MUST-SEE, 1 CAR GARAGE USED AS A STORAGE ROOM, CERAMIC TILE AND PORCELAIN TILE THROUGHOUT THE WHOLE HOUSE, ROOF 1 YEAR OLD, NEWER AC, CLOSE TO SHOPPING CENTERS, SCHOOLS, BUS LINE, CLINICS, SHORT DRIVE TO DOWNTOWN SARASOTA, SIESTA KEY, RINGLING MUSEUM, UTC MALL, MARINA JACKS, LIDO BEACH, SAINT ARMANDS. BUYER OR BUYER'S AGENT TO VERIFY ALL MEASUREMENTS; WE TRY TO PROVIDE THE BEST INFORMATION AVAILABLE TO OUR OFFICE.

537 Melody Circle, Mid Town Sarasota

$270,000

3 Beds ⋅ 2 Baths ⋅ A4697851 MLS ⋅ 1010 BLDG.

You can move in immediately or rent right away for everything you could need is included - furniture, decor, window treatments, kitchen service items, sheets, towels, porch furniture and pillows, all appliances. This is truly turnkey! Three bedroom units are coveted and particularly when they include a deeded carport for parking. The has been beautifully remodeled with granite countertops, luxury linoleum throughout, and all furniture and decor to match the Florida coastal lifestyle. The buildings are only two stories high and this condo is on the second floor eliminating any issues of pedestrian or car traffic directly in front of your windows or any potential rising water. Villagio has remained a community in high demand due to its proximity to downtown Sarasota, the spring training stadium for the Baltimore Orioles, sporting parks, independent restaurants and stores, grocery, schools, and public transportation. Villagio is a gated community with a pool, fitness room, clubhouse, pool, tennis and pickleball courts, a small putting green, designated dog area, and green space with picnic tables. It remains a wonderful place to live full-time, seasonally, or as a rental investment (one month minimum, maximum 3 times per year). Pet and all age-friendly.

1010 Villagio Circle Unit 201, Mid Town Sarasota

$1,129,000

3 Beds ⋅ 4 Baths ⋅ TB8523163 MLS ⋅ Building 1 BLDG.

Luxury Downtown Sarasota Townhome | Main Street | Private Elevator | Rooftop Terrace | Main-Floor Lockout Suite | Two-Car Parking - Experience contemporary luxury and exceptional flexibility in this distinctive four-story Downtown Sarasota townhome, built in 2023 and offering approximately 2,350 square feet of thoughtfully designed living space. Located directly on Main Street, the home features a private main-floor lockout suite with a full bath and its own access to Main Street, offering a rare combination of privacy, flexibility, and versatility for guests, multigenerational living, a private home office, fitness studio, or potential income-producing use. A private elevator serves every level, while dedicated two-car parking in the rear alley provides convenient off-street parking in the heart of downtown. The residence showcases elegant porcelain flooring, dramatic floating wood staircases with sleek glass railings, soaring ceilings, and refined contemporary finishes throughout. The open-concept living level is designed for both everyday living and entertaining, with a gourmet kitchen featuring Frigidaire Gallery appliances, Electrolux vented hood, gas cooktop, convection double ovens, soft-close cabinetry, abundant storage, and seamless connection to the living and dining areas. Outdoor living is an exceptional extension of the home, with a private rooftop terrace designed for relaxing, entertaining, and enjoying Sarasota’s year-round sunshine. The rooftop terrace features a private outdoor kitchen with gas plumbing and sink, creating an ideal setting for al fresco dining, cocktails, or gatherings with friends and family. The combination of private rooftop living, newer 2023 construction, and a low-maintenance design allows you to spend more time enjoying everything Downtown Sarasota has to offer. Ideally positioned on Main Street in the heart of Downtown Sarasota, this luxury townhome places the city’s best dining, shopping, arts, entertainment, and waterfront attractions just outside your door. Walk to acclaimed restaurants, upscale boutiques, galleries, coffee shops, rooftop lounges, the Sarasota Opera, live theater, weekend farmers markets, Marina Jack, Bayfront Park, and Sarasota Bay. Enjoy morning walks along the waterfront, afternoons exploring Main Street and Palm Avenue, and evenings experiencing the city’s vibrant dining and cultural scene—all with the convenience of leaving your car at home. When it’s time for the beach, Lido Key, St. Armands Circle, Longboat Key, and Sarasota’s renowned white-sand beaches are just minutes away. Whether envisioned as a primary residence, elegant seasonal retreat, or flexible investment property, this distinctive luxury townhome combines modern construction, private outdoor living, flexible accommodations, and an exceptionally walkable downtown location. A rare opportunity to own a newer luxury townhome directly on Main Street in the heart of Downtown Sarasota, where sophisticated urban living and the Gulf Coast lifestyle come together. New listing agent and price, updated pictures and 3D tour coming soon!

2187 Main Street, Mid Town Sarasota

$97,000

1 Beds ⋅ 1 Baths ⋅ A4696863 MLS ⋅ 2613 BLDG.

Location! Location! Location! Close to all the amenities in beautiful Sarasota. Great investment plan or place to call home!

2613 Pine Lake Ter Unit B, Mid Town Sarasota

$97,000

1 Beds ⋅ 1 Baths ⋅ A4696861 MLS ⋅ 2632 BLDG.

Location location location! Close to all the amenities of beautiful Sarasota. A great place to bask in the Florida sunshine! The South side of the unit faces the lake.

2632 Hidden Lake Dr N Unit B, Mid Town Sarasota

Mid Town Sarasota Homes with Booker High High School

Newest Mid Town Sarasota Homes with Booker High High School