Siesta Key Investment Properties For Sale

Commercial Real Estate in Siesta Key available for sale

Investment Properties for Sale in Siesta Key, FL, USA

More details for 5322 Calle de la Siesta, Sarasota, FL - Hospitality for Sale

Siesta Sunset Royale, a 7-unit nightly rental - 5322 Calle de la Siesta

Sarasota, FL 34242

Investment Property
Hospitality for Sale
$6,773,760 CAD
4,534 SF

Pool

Sarasota Hospitality for Sale

Nightly rentals, a unicorn. This 7-unit investment property is unique in that it operates more similar to hotel than a single family vacation rental. It has years of returning guests and it's one of very few elevated properties allowing the former mentioned, nightly rentals. 2-studios, 2-1 bedrooms, 2-2 bedrooms, and a penthouse suite with wrap around balcony. Your guests will enjoy a great pool area, sizable covered space with a grill, on site laundry, and a roof top deck. It's 1 block to both the Village and beach, guests walk everywhere. Park your car in one of the 7 newly pavered spaces and don't start it again until the vacation is over. Now for you the owner, a private office/guest check in, 2 storage areas for linens housewares etc, and a commercial laundry for turnovers. These types never trade, don't let another 20 years pass before this sells again.

Contact:

Compass

Property Subtype:

Serviced Apartment

Date on Market:

2026-02-12

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More details for 1150 Windsong Ln, Siesta Key, FL - Land for Sale

Azure Siesta Key - 1150 Windsong Ln

Siesta Key, FL 34242

Investment Property
Land for Sale
$3,110,400 CAD
0.23 AC Lot

Siesta Key Land for Sale - Sarasota

Prime development opportunity with plenty of upside in one of the country's premier vacation destinations.

Contact:

TC Group, LLC

Property Subtype:

Commercial

Date on Market:

2021-08-18

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Investment Properties for Sale within 10 kilometers of Siesta Key, FL, USA

1610 22nd St

Sarasota, FL 34234

Investment Property
Multifamily for Sale
$593,050 CAD
1,625 SF

Sarasota Multifamily for Sale

This well-maintained duplex is ideally situated just minutes from the airport, downtown Sarasota, and the area's world-renowned beaches. The property features two separately metered units, offering strong rental appeal and ease of management: Unit 1: 3 bedrooms, 1 bathroom Unit 2: 2 bedrooms, 1 bathroom Both units are tenant-occupied with long-term leases in place, generating a gross monthly rent of $3,350. Tenants pay their own water and electric, keeping operating expenses low for the owner. Situated on a desirable corner lot, the property also includes laundry hookups for added tenant convenience. Major updates have already been completed, providing peace of mind for investors: Newer roof Updated central A/C units Upgraded electrical and plumbing systems Unique Financing Opportunity: The seller is open to creative financing options and currently has a mortgage on the property, making this an excellent opportunity for buyers seeking flexible terms.

Contact:

Blue Peak Realty

Property Subtype:

Multi Family

Date on Market:

2026-04-15

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1860 7th St

Sarasota, FL 34236

Investment Property
Specialty for Sale
$1,035,418 CAD
1,568 SF

Air Conditioning

Sarasota Specialty for Sale

This Gillespie Park duplex presents a compelling investment opportunity in the heart of Sarasota’s vibrant downtown neighborhood. The property consists of two well-maintained two-bedroom, one-bath residences totaling approximately 1,568 square feet on a 7,500-square-foot lot. Both units are configured for rental income, offering immediate cash flow potential. The front unit features a long-term tenant, ensuring occupancy stability, while the rear unit is ready for short-term or long-term leasing strategies. Recent capital improvements include a new roof installed in 2017, updated sewer and water lines within the past three years, and modern enhancements to both residences. The DTN (Downtown Neighborhood) zoning allows for redevelopment potential subject to city approvals, making this property attractive for investors seeking future upside. Located directly across from the 10-acre Gillespie Park and within walking distance to downtown Sarasota, residents enjoy proximity to cultural venues, dining, shopping, and waterfront attractions. With Payne Park, the Legacy Trail, and numerous recreational amenities nearby, this property combines income-producing capability with long-term growth prospects in one of Sarasota’s most desirable neighborhoods.

Contact:

Premier Sothebys International Realty

Property Subtype:

Residential Income

Date on Market:

2026-04-07

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More details for 530-536 S Pineapple Ave, Sarasota, FL - Retail for Sale

The Historic Pineapple Apartments - 530-536 S Pineapple Ave

Sarasota, FL 34236

Investment Property
Retail for Sale
$11,750,400 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

Investment Property
Retail for Sale
$2,073,462 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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More details for 2119- 2125 Montclair Dr, Sarasota, FL - Multifamily for Sale

2119-2125 Montclair - 2119- 2125 Montclair Dr

Sarasota, FL 34231

Investment Property
Multifamily for Sale
$1,465,344 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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Residential Assemblage Near Siesta Key

Investment Property
Mixed Types for Sale
$3,070,310 CAD
3 Properties | Mixed Types

Sarasota Portfolio of properties for Sale

American Property Group of Sarasota, Inc. presents 3 Unit Residential Assemblage near Siesta Key Zoning: RSF-1 Total Lot Size: 38,301 SF (Three parcels totaling 12,767 SF each) Rare opportunity to acquire three adjacent residential parcels located on Southpointe Dr in Sarasota, just minutes from the world-famous Siesta Key beaches. This unique assemblage includes a duplex, a single-family home, and a vacant lot; offering flexibility for personal use, investment income, or future redevelopment. You can build your dream home with water views easily with a huge yard, easy access to many established local businesses, schools, grocery stores and more, all just a few minutes from Siesta Key Beach! 1. Duplex – 1,993 SF 1860 Southpointe Dr, Sarasota, FL This well-maintained two-family dwelling features two spacious 2 bedroom, 2 bathroom units, making it ideal for investors or multi-generational living. The property includes a rare RV full hookup pad, a two-car garage, and access to a community boat dock, enhancing its versatility and rental appeal. Its location and features make it a prime opportunity for those seeking strong income potential in Sarasota’s hot residential market. 2. Single-Family Home – 1,852 SF 1848 Southpointe Dr, Sarasota, FL Charming and versatile, this 4 bedroom, 3 bathroom home offers generous interior space and unique potential for customization or expansion. The home features a private screened-in in-ground pool; perfect for relaxing or entertaining in the Florida sunshine. With access to the same community boat dock as the neighboring parcels, it serves as an ideal primary residence, vacation home, or rental property. 3. Vacant Residential Lot – 12,767 SF 0 Southpointe Dr, Sarasota, FL Ready for development or held for future investment, this buildable lot shares RSF-1 zoning and offers direct adjacency to the existing homes; perfect for a custom home, guest house, or expansion of your portfolio. Each property is available individually or all three can be purchased together as a package.

Contact:

American Property Group of Sarasota, Inc.

Property Subtype:

Mixed Types

Date on Market:

2025-07-29

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