Mid Town Sarasota Real Estate

Mid Town Sarasota Real Estate

Midtown Sarasota is a vibrant and charming neighborhood located in Sarasota County, Florida. Situated in the heart of the state, Midtown Sarasota offers a perfect blend of urban convenience and natural beauty.

As part of Sarasota County, residents of Midtown Sarasota have access to a wide range of amenities and attractions. The area boasts a thriving arts and culture scene, with numerous galleries, theaters, and museums to explore. From contemporary art exhibits to live performances, there is always something exciting happening in Midtown Sarasota.

Nature enthusiasts will also find plenty to enjoy in this area. The neighborhood is surrounded by beautiful parks and green spaces, perfect for outdoor activities like hiking, biking, and picnicking. Just a short drive away, residents can also access the stunning beaches of the Gulf Coast, where they can soak up the sun, swim in the crystal-clear waters, or indulge in water sports.

In addition to its natural beauty and cultural offerings, Midtown Sarasota is also known for its diverse dining and shopping options. From trendy boutiques to gourmet restaurants, there is something to satisfy every taste and preference.

With its convenient location and abundance of amenities, Midtown Sarasota is a wonderful place to call home. Whether you are looking for a peaceful retreat or an exciting urban lifestyle, this neighborhood has it all.

Newest Listings in Mid Town Sarasota

6 Beds ⋅ 6 Baths ⋅ TB8541085 MLS

Rare Sarasota duplex opportunity with a private swimming pool and exceptional flexibility for investors, multigenerational living, or an owner-occupant looking to generate rental income! Tucked away on a quiet cul-de-sac, 1213/1215 Benedict Ct offers two spacious units with a total of 6 bedrooms and 6 full bathrooms. Each unit features 3 bedrooms and 3 full baths, with every bedroom having access to its own full bathroom—an ideal layout for privacy, guests, extended family, or rental use. The property also offers mother-in-law suite functionality with a kitchenette for additional flexibility. One unit has been beautifully renovated, including an extensively renovated kitchen in approximately 2021, and is being offered fully furnished for a potential turnkey rental opportunity. Seller represents roof was replaced in approximately 2017; buyer to verify permitting, age and condition. Enjoy the Florida lifestyle with a private swimming pool and patio area perfect for relaxing and entertaining. Additional highlights include two separate addresses and a versatile duplex configuration. Conveniently located near Downtown Sarasota with easy access to shopping, dining, entertainment, and Sarasota's world-famous Gulf Coast beaches. The property offers excellent potential for traditional, furnished, or short-term vacation rental use, subject to applicable City of Sarasota requirements. Live in one side and rent the other, accommodate extended family, or add a versatile Sarasota income property to your portfolio. Buyer and buyer's agent to verify room configuration, permitting, rental requirements, measurements, and all information deemed important to buyer.

1213 Benedict Court, Mid Town Sarasota

5 Beds ⋅ 5 Baths ⋅ A4702740 MLS

Pre-Construction. To be built. Experience the best of the Sarasota lifestyle in this thoughtfully designed modern residence, created for effortless Florida living, entertaining and flexibility. Offering 5 bedrooms plus a versatile bonus room, 4.5 bathrooms, 2,900 sqft of air-conditioned living space and 3,389 total sqft, the home combines contemporary architecture with a highly functional floor plan. At the heart of the residence, expansive open-concept living spaces flow seamlessly to the outdoors, creating an ideal setting for both everyday living and entertaining. The private outdoor retreat features a pool, outdoor kitchen and outdoor shower, perfect for sun-filled afternoons, weekend gatherings and evenings spent dining poolside. A two-car garage and flexible bonus room provide additional space for guests, a home office, fitness room, media room or playroom. Located within the City of Sarasota, the property offers convenient access to Downtown Sarasota’s acclaimed dining, shopping, arts and entertainment, while remaining just a short drive from the area’s renowned Gulf Coast beaches. Enjoy nearby access to the Legacy Trail, Sarasota’s parks, waterfront destinations and everything that makes the city one of Florida’s most desirable places to live. Adding to its appeal is the property’s potential for short-term rental use, creating flexibility for buyers seeking a primary residence, vacation retreat or income-producing investment. Whether enjoyed as a full-time home or a private Florida escape, this residence offers a compelling combination of modern design, resort-style amenities, location and lifestyle.

2350 Bay St, Mid Town Sarasota

3 Beds ⋅ 1 Baths ⋅ A4703343 MLS

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

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

3 Beds ⋅ 2 Baths ⋅ A4701083 MLS

NOW is the time to BUY! Excellent VALUE with all the upgrades in this unit. Call for an appointment to see it today. UPDATED kitchen with Shaker, soft-close cabinets, quartz countertop, stainless appliances. Updated bathroom vanities and showers. High-impact windows. Screened-in Lanai. Private backyard. Carport with a storage area. Exterior and interior painting 2026. Roof and exterior maintained by the Association. If you have pets, 1 dog and 2 indoor cats allowed. Meet your neighbors at the Community Pool and Clubhouse. This 55+ Sarasota community embraces 46 acres with Spanish Moss-covered trees in a park-like setting. LOCATED a short distance to downtown Sarasota, University Town Center (UTC), great restaurants and shopping, sandy Lido Beach and Siesta Beach, various theatres, SRQ Airport and other Sarasota cultural and sports amenities. Schedule your showing today to buy now at a GREAT PRICE, and you, too, can experience a low-maintenance Florida LIFESTYLE!

1554 Tallywood Drive Unit 7127, Mid Town Sarasota

2 Beds ⋅ 2 Baths ⋅ A4703239 MLS ⋅ 19 BLDG.

Just a few minutes from downtown. Move in ready ground-floor, 2-bedroom, 2-bathroom condo is just minutes from downtown Sarasota. Located in a private, wooded, and deed-restricted community, the condo features a sleek interior with granite countertops, a breakfast bar, tile and laminate wood floors, vaulted ceilings, and ceiling fans. The rear lanai offers a view of a wooded area with a partial lake view. Tenant occupied paying $1,845/ month.

630 N Jefferson Avenue Unit 19, Mid Town Sarasota

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

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

3 Beds ⋅ 2 Baths ⋅ TB8538039 MLS

Reimagined from top to bottom under a fully permitted renovation, completed in 2021- This move-in-ready home blends modern updates with an unbeatable location on a quiet dead-end street. The open-concept layout is anchored by a kitchen featuring custom cabinetry, a large island and granite countertops, with a full suite of Samsung stainless steel appliances. Two sliding doors provide access to a fully screened lanai where you can relax, overlooking a fenced yard that opens onto a wide green corridor along the west side-offering exceptional sunset views and privacy. Both the primary en suite and guest bathrooms feature custom vanities with quartz tops. Big-ticket items are completely done: hurricane impact window and doors throughout, full interior re-pipe, upgraded electrical panel, luxury vinyl flooring throughout, 2019 Roof, 2018 HVAC, and 2021 water heater make this property a real standout with a rare combination of upgrades and updates. The renovation included full interior and exterior paint, all-new doors and sliders, new garage door and opener with a battery back-up. Smart-homes features include a smart thermostat, video doorbell and keyless entry controlled with a hub or smartphone. Ideally located just minutes from downtown Sarasota, the Bayfront, and world-famous Siesta Key beaches. With strong rental and resale fundamentals in a fast-appreciating ZIP, this turnkey home is ready for its next owner. Schedule your showing today!

2874 Davis Boulevard, Mid Town Sarasota

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

5 Beds ⋅ 3 Baths ⋅ A4702086 MLS

This property is gem in the rough, so close to downtown Sarasota and the Bay with a mixed-use zoning DTN, which falls under the Downtown Master Plan of 2020. Compared with conventional zoning that encourages development of Urban Communities that are diverse, compact and walkable. Plenty of possibilities in usage, height and added outbuildings. The current use is residential income producing with two units. Check this out, make future plans and be part of the Sarasota growth.

632/634 N East Avenue, Mid Town Sarasota

2 Beds ⋅ 2 Baths ⋅ A4702390 MLS

OAKWOOD MANOR — WHERE FUN AND FRIENDSHIPS BEGIN! LOW-MAINTENANCE LIVING IN A HIGH-VALUE LOCATION ** Welcome to Oakwood Manor, Sarasota’s only resident-owned 55+ community within the Sarasota city limits—where affordability meets an active, social lifestyle. This 2-bedroom, 1.5-bath home offers 749 sq. ft. of living space and sits on a desirable oversized lot (50 x 80.5), giving you extra room and exciting potential. A spacious covered and screened Florida room welcomes you at the front of the home—perfect for morning coffee, entertaining guests, or simply enjoying the Florida lifestyle year-round. Major Updates Already Done: ** A/C replaced in 2020 ** Roof replaced in 2023, new flooring through out 2026, new Kitchen, new baths and half bath and newly painted interior. Oakwood Manor spans 90 beautifully maintained acres and is known for its low maintenance fees and friendly, welcoming atmosphere. Community Amenities Include: ** Clubhouse with fitness room, dance floor & library ** Heated pool & hot tub ** Putt-putt golf, bocce ball, shuffleboard & cornhole ** Ping-pong & pool table ** Shaded seating areas & picnic park with grill ** Full calendar of social events and activities Love pickleball? Courts are just a short bike ride away along the Legacy Trail, located right next to the community. You’re also just minutes from downtown Sarasota, Gulf beaches, shopping, dining, and major hospitals—everything you need, right at your fingertips. Note: no pets, motorcycles or trucks community

3415 Spanish Oak Terrace, Mid Town Sarasota

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