The Historic Pineapple Apartments - 530-536 S Pineapple Ave

Sarasota, FL 34236

• Airbnb Property
• Retail for Sale
• $11,649,590 CAD
• 13,761 SF

• Air Conditioning
• 24 Hour Access
• Restaurant

Sarasota Retail for Sale

The Historic Pineapple Apartments, the centerpiece of Burns Square. This building has deep ties to Sarasota history, built by Owen Burns (our city's first developer) in 1925. Last purchased in 1986, you will never walk a more curated and cared-for building. It's a step back into the Roaring '20s and a modern-day reminder that community is local. At one time an apartment building, it now serves as a thriving vacation rental. It has 8 suites (could be 13), 7 retail shops below, and a 3,000 sq ft owner's suite. Wrought-iron balconies align the exterior walls, Venetian plaster the interiors, multiple exposed beams, and a historical monument next to the fountain at Little Five Points. It's Sarasota's "Flatiron Building," triangulated architecture, impossible to go unnoticed. It is the entrance to downtown from the south, a beacon, a landmark for our great city.

Contact:

Compass

Property Subtype:

Storefront Retail/Residential

Date on Market:

2026-03-16

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3351 Bahia Vista St

Sarasota, FL 34239

• Airbnb Property
• Retail for Sale
• $2,055,673 CAD
• 2,400 SF

Sarasota Retail for Sale

: LOCATION, LOCATION, LOCATION! Rare commercial/residential opportunity! Come see this hidden gem, an income-producing property not available since the sixties, located in the heart of Pinecraft, Sarasota’s Amish-Mennonite community! Live, work or retire at this charming property in Sarasota County, one of Florida’s most desired relocation destinations on the Gulf Coast, and one of the prettiest areas of Florida. Centrally located between I 75 and US 41 in Sarasota County, just outside city limits, Pinecraft is a safe community for walking and biking. The famous Legacy Trail winds through Pinecraft and Breeze public transit stops nearby on Bahia Vista Street, making shopping and sightseeing very accessible for those who prefer biking. It is also only six miles to the beautiful sandy sands of world-renowned Siesta Key and Gulf of America, and two miles to the Sarasota Bay for all those avid sea lovers who enjoy fishing, shelling and sunsets. Pinecraft Market is an excellent family-owned home-business location for nearly 60 years in the downtown square of Pinecraft, with road frontage on high-traffic Bahia Vista Street. It’s best-use value is its commercial zoning, with Pinecraft real estate continually in high demand, based on availability rather than comps. The adjoining businesses at the Bahia Vista and Kaufman intersection are Yoder’s Restaurant & Deli, Pinecraft Icecream and Pizza Shoppe and Postal Café, Everence Credit Union and Pinecraft Golf shop and Loretta’s Doughnuts. Pinecraft overflows in the winter season with tourists and winter residents, creating an instant business opportunity, while the increasing amount of relocators to Sarasota keep the local businesses flourishing year-round. The highly desirable feature of the property is the grandfathered zoning which allows for commercial and residential uses simultaneously, the only business in the Pinecraft square with this feature! Endless possibilities! Need an Airbnb? Or leasable units for residential rentals? Or leasable commercial space, or an operating family-owned business? Or a 1031 exchange for that piece of property you just sold? Or invest in a winter home or an inheritance for your grandchildren? Produce market? Bookstore and coffee shop? Local Arts & Crafts Shop? Massage therapy? Open-air Smoothie business or bubba tea stand? Wellness clinic? Counseling center? Ministry retreat? R&R vacation property to avoid employee burnout? Historical Society or information center? Or simply a place to enjoy southern living while bringing in an income through rentals? Bring your dreams to life!

Contact:

Premier Plus Realty

Property Subtype:

Storefront

Date on Market:

2026-02-19

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1345 2nd St

Sarasota, FL 34236

• Airbnb Property
• Office for Sale
• $5,208,052 CAD
• 8,165 SF

• Air Conditioning
• Natural Light
• Security System
• Kitchen
• Reception
• Roof Terrace

Sarasota Office for Sale

RARE OPPORTUNITY to purchase a mixed use building in the heart of Downtown Sarasota. This exceptional three-story mixed used building offers an unparalleled blend of luxury and convenience. With a prime location just steps from premier dining, shopping, and cultural attractions, this unique property invites you to embrace city living at its finest. Constructed in 2000, the first floor welcomes visitors with a bright, coastal-inspired entrance, featuring luxury vinyl plank flooring in a light oak finish. This level includes a spacious open area with an abundance of natural light pouring in. This floor was previously a salon sitting 12 stations, 6 wash stations, 4 drying stations, along with 2 well-appointed bathrooms. The salon area has a state of the art mixing station, accented by high-end sleek dark tile. Upstairs, accessible by both staircase and elevator, you'll find 7 generously sized treatment rooms with plumbing, 2 additional bathrooms, a dedicated breakroom, and an office. One of the standout features is a unique room with a stunning wall crafted from Himalayan salt bricks, adding a luxurious and tranquil touch. The second floor also includes a naturally well lit break room that accommodates both the first and second floor. Ascend to the private penthouse on the 3rd Floor via the private access elevator and discover a breathtaking four-bedroom residence designed for modern sophistication. The expansive open floor plan is accentuated by soaring ceilings and abundant natural light streaming through floor-to-ceiling windows. The chef’s kitchen is a masterpiece, featuring a grand island, wine fridge, built-in oven and microwave, and a six-burner gas cooktop with a dedicated grilling area. A separate full-length wet bar and coffee station, complete with two dishwashers and ample storage makes this private residence perfect entertaining. The seamless flow between the dining and living areas—anchored by a soothing fireplace—creates a warm and inviting atmosphere. Step outside onto the private balcony off the kitchen, where city views provide a picturesque backdrop for dining and entertaining A space perfectly designed for gardening or grilling out with friends. A striking spiral staircase leads to the third-floor bedroom with an en-suite half-bath and its own rooftop terrace for a tranquil retreat. This space is currently being used as a short term rental. The building offers two assigned covered parking spaces. This is a great opportunity for an owner occupier to run their dream business while living above. The building is being sold as vacant however the med spa on the 2nd floor would consider staying on a long term lease. Schedule a private showing today to learn more about this opportunity!

Contact:

Compass Florida

Property Subtype:

Office/Residential

Date on Market:

2026-01-26

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2119-2125 Montclair - 2119- 2125 Montclair Dr

Sarasota, FL 34231

• Airbnb Property
• Multifamily for Sale
• $1,452,772 CAD
• 2,731 SF

• Air Conditioning
• Pool

Sarasota Multifamily for Sale

PRICE REDUCTION!! | View Offering Memorandum document at MultifamilyFirm.com for full details!! ** Property being offered individually or as a Portfolio w/ the adjacent Duplex property (2131 Montclair) *** The Multifamily Firm is pleased to present 2119-2125 Montclair, a premier investment opportunity located in the quietly desirable enclave of Coquina Island, just minutes from Siesta Key Beach in Sarasota, Florida. Built in 2007 with durable masonry construction and situated in a non-flood zone, the property consists of two spacious, townhome-style units, each featuring 3-Bedrooms, 2.5-Bathrooms, a private swimming pool (one screened-in), a two-car garage, a screened patio, and a private yard. The design offers a single-family home feel with the efficiency and scale of multifamily ownership. From an operational standpoint, all utilities are separately metered and paid directly by tenants, significantly reducing owner expenses and improving overall cash flow. The property’s layout consists of three separate parcels: two individually deeded parcels for the residential units and a third parcel for the shared common area. This configuration gives investors strategic flexibility to hold the asset as a traditional duplex or pursue a condo exit strategy by selling the units individually. Given its close proximity to Siesta Key, the property is also well-positioned for short-term vacation rental use, presenting multiple paths to maximize returns. With quality construction, minimal overhead, and built-in optionality, 2119-2125 Montclair offers an ideal blend of lifestyle appeal and long-term investment upside. View Offering Memorandum for full details & financial information at MultifamilyFirm.com

Contact:

The Multifamily Firm, LLC

Property Subtype:

Apartment

Date on Market:

2025-06-13

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