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$8,500,000
10 Beds ⋅ 13 Baths ⋅ Burns Owen SubDv. ⋅ 34236 Zip Code
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.

530 S Orange Avenue, Sarasota
$4,400,000
9 Beds ⋅ 11 Baths ⋅ Siesta Sunset SubDv. ⋅ 34242 Zip Code
5.9% Seller Financing and 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. Cap rate and NOI is proforma

5322 Calle De La Siesta, Sarasota
$3,995,000
4 Beds ⋅ 4 Baths ⋅ Golden Gate Point SubDv. ⋅ 34236 Zip Code
One of the Last Remaining Legacy Properties on Golden Gate Point | Rare Trophy Ownership, Redevelopment & Strategic Hold Opportunity A truly rare offering in one of Sarasota’s most exclusive and rapidly evolving luxury enclaves. With no true single-family homes currently remaining on Golden Gate Point and only a small handful of original legacy properties left, 161 Golden Gate Point represents one of the final opportunities to control a meaningful piece of “old Golden Gate” before the peninsula is fully transformed. Positioned in the heart of downtown Sarasota, across from the Ritz-Carlton and adjacent to Marina Jack, the property currently consists of a fully updated Four-unit building featuring newer central A/Cs, five-piece stainless kitchens, quartz countertops, new roof (2025), separate electrical meters, gated courtyards, hot tub, and gazebo — offering immediate usability and meaningful interim income while future plans are explored. Located within the City of Sarasota weekly vacation rental zone, this creates a rare opportunity not commonly found in downtown Sarasota — operate the property similarly to a boutique hotel. For the visionary buyer, this may represent a once-in-a-generation opportunity to create what could become Golden Gate Point’s only true single-family estate — a one-of-one trophy residence in the heart of downtown Sarasota. The property also presents compelling redevelopment potential. Golden Gate Point benefits from alternative development standards intended to support a more urban, pedestrian-friendly environment, including reduced setbacks, increased building coverage allowances, and flexible dimensional standards — enhancing redevelopment possibilities in this highly sought-after peninsula location. Similar RMF-5 sites on Golden Gate Point have supported boutique luxury residential concepts, while the adjacent rear assemblage totaling approximately 21,600 SF is also available, creating a rare opportunity for a larger strategic assemblage in one of Sarasota’s most supply-constrained luxury micro-markets. 161 also represents a compelling long-term hold opportunity. As Golden Gate Point continues its luxury transformation — and remaining legacy properties disappear — the opportunity to control irreplaceable downtown Sarasota land becomes increasingly rare. Just moments to Marina Jack, downtown Sarasota dining, St. Armands Circle, Lido Beach, and Sarasota’s transformative bayfront destination, The Bay. Whether envisioned as: • Rare short-term rental building where you control the entire property • One of Golden Gate Point’s final legacy holdings • A future one-of-one single-family estate • A boutique luxury redevelopment site • A strategic assemblage opportunity • A family office or long-term scarcity hold • Or a rare downtown Sarasota land play with meaningful interim income potential …opportunities of this nature are becoming increasingly difficult to replicate.

161 Golden Gate Point, Sarasota
$3,899,000
Halls Sub James S SubDv. ⋅ 34236 Zip Code
Pre-Construction. To be built. INVESTOR - DEVELOPER OPPORTUNITY in Rosemary District on Orange Ave! Three Lots permitted for five story, 18 unit condos. Orange Ave is a thriving corridor from Downtown to Rosemary with recently finished projects with this one to be a highlight to the street. Flanked by the Sarasota Military Academy to the North and Citrus Square to the South, this opportunity is positioned in a spectacular and convenient location. Distance to Main St - Downtown 0.4 miles Distance to Sarasota Airport (SRQ) 3.8 miles Distance to Ringling College 1.7 miles The prime benefit to buyer is “time”, team has worked for over a year and have APPROVED Civil Plans from City of Sarasota and development team is working on construction drawings to be submitted for approval, this project is 60-90 days away from shovel ready.

711 N Orange Avenue, Sarasota
$3,350,000
Siesta SubDv. ⋅ 34242 Zip Code
Discover Unrivaled Coastal Elegance Steps from Siesta Key Beach! This rare gem features two meticulously remodeled canal-front homes with stunning partial views of the bay, perfectly situated in a prestigious neighborhood. The main residence boasts a contemporary design with open and spacious layouts, highlighted by soaring 24 ft ceilings adorned with stylish gray wooden accent beams. Culinary enthusiasts will be captivated by the gourmet kitchen, featuring custom-made wood cabinets complemented by exquisite Carrara Quartz countertops. Equipped with top-of-the-line appliances, including a new stainless Thermador refrigerator, Bosch dishwasher, and an impressive center island with a bar area, it truly caters to the most discerning chefs. Zoned RMF2 while located in a single-family neighborhood, this property allows for daily Airbnb rentals, making it an excellent investment opportunity. A private, charming guest cottage serves as an ideal retreat or rental for additional cash flow. Recent upgrades include new Window World Hurricane-rated windows, French doors, and a newly installed seawall (2025), ensuring your investment remains safe and secure. The main house spans 3,005 sq ft, featuring three bedrooms and 2.5 baths adorned with luxurious Panaria marble and 24x48 tile flooring. Bathrooms boast contemporary Miseno vanities and premium Grohe and Hansgrohe fixtures. The decadent master suite invites relaxation with a rain cap shower and a sumptuous soaking tub. Both homes are equipped with new Rheem A/C units, while the property’s outdoor oasis features a large screened lanai overlooking the canal and bay. Dive into the newly resurfaced pool with a stunning stone waterfall or enjoy the expansive outdoor space, surrounded by tropical landscaping. The cozy guest cottage, covering 1,700 sq ft, includes three bedrooms and two full baths, showcasing beach-washed ceramic tile flooring, white wood Shaker cabinets, and modern KitchenAid and Bosch appliances. The new dock provides easy access to pristine boating waters with no bridges obstructing your path to the bay. Siesta Key is a haven for music lovers and foodies alike, while Sarasota delights with its vibrant art scene, ballet performances, the Asolo Performing Arts Center, the Ringling Art Museum, and world-class shopping. Relax with your favorite beverage on the rear patio, shaded by a majestic live oak, or grab your fishing rod, bathing suit, and water toys to fully embrace the Siesta Salt Life. Act fast! This exquisite property offers a luxurious lifestyle and lucrative potential in one of Florida’s most sought-after destinations!

1240 Solitude Lane, Sarasota
$3,195,000
4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Discover an exceptional income-generating property in the heart of coveted Siesta Key right on Beach Road! This fully renovated raised multi-unit compound features a spacious 2-bedroom, 2-bathroom unit and a 2-bedroom, 1-bathrooom unit (side by side). An impressive gross income in 2023 and n 2024 (despite hurricane-related downtime), this turnkey investment provides immediate cash flow. Note: This property is zoned an RMF (Residential Multifamily) and is legally able to accept nightly rentals. The property boasts recent upgrades including new AC (2022), updated flooring (2025), modernized plumbing (2022), electrical (2022), and hot tubs (2022). This amazing opportunity is the best cap rate on any house on Siesta Key. Whether you're seeking a high-performing Airbnb rental portfolio or a strategic redevelopment opportunity in one of Florida's most desirable beach destinations, this property delivers both immediate income and long-term appreciation potential. Absentee owner managed; turnkey operation available at on a management fee with all staff staying in place. This house already has engineering drawings to enclose the bottom area adding 2,000 additonal square foot, that would increase rent by or more. This property could be purchased as a portfolio with 5228 Calle Menorca and 6550 Sabal Road.

527 Beach Road, Sarasota
$2,895,000
5 Beds ⋅ 7 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

Sarasota
$2,895,000
5 Beds ⋅ 7 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.

6910 Midnight Pass Road Unit B, Sarasota
$2,529,000
32 Beds ⋅ 16 Baths ⋅ James Street Park SubDv. ⋅ 34236 Zip Code
SARASOTA ~ CITY OF SARASOTA ~ ROSEMARY DISTRICT ~ DOWNTOWN LIVING AND / OR INVESTMENT, WITH UPSIDE DEVELOPMENT OPPORTUNITIES! - WE ARE SELLING 4 CONTIGUOUS PROPERTIES WITH FOUR RENTAL HOMES ON AN ESTIMATED 23K SF +/- LAND!!!! Come and explore this unique opportunity to own and operate four contiguous properties with homes within the much sought after City of Sarasota "Rosemary District". The current rent roll is estimated at $100K +/-, all the current homes (4) are rented on an annual basis. The zoning does allow for short term weekly rentals, come and set up your own short term rental compound with estimated average daily rates @ $50.00 - $100.00 +/. Want another reason to look, owner will consider "owner financing" and/or selling off less then all four homes. There are just not many opportunities in the City of Sarasota to secure rezoned lands with the ability to use the current as-is property to secure carry income while waiting for the right timing to develop. The upside development in the Rosemary Zoning District: up to 7-stories with up to 30+ units. Property is very easy to show, sign is on site! NOTE: another contiguous parcel - rental home available for discussion. NOTE: future development plans viable on request!

1555 7th Street, Sarasota
$2,200,000
8 Beds ⋅ 5 Baths ⋅ Shenandoah Park SubDv. ⋅ 34237 Zip Code
This centrally located, five-parcel assemblage in Sarasota’s Park East neighborhood offers a rare redevelopment opportunity in an area experiencing ongoing growth. Totaling approximately 35,000 square feet (350 road frontage x 100) deep or (0.80 acres), the site currently includes five income- producing rental units bringing in a total of $8,250 per month. The property is also situated within an Opportunity Zone. Zoning allows for mixed-use development with ground-floor commercial and multifamily residential uses as well as hotel developments with ground-floor commercial. The property supports a base density of 25 units per acre, with the potential to achieve up to 100 units per acre through participation in the City of Sarasota’s Attainable Housing Density Bonus Program. Building heights of up to four stories are permitted under current zoning. The property is strategically located near downtown Sarasota, US-301, Fruitville Road, and I-75, offering convenient access to local employers, retail corridors, and regional transportation. Nearby recreational and cultural amenities include Bayfront Park, Payne Park, Gillespie Park, and the Rosemary District. Rental income provides holding revenue while entitlements and development planning are pursued. Buyer is responsible for verifying all zoning regulations, density bonuses, and development entitlements with the City of Sarasota.

2050-2026 10th, Sarasota
$1,600,000
Valencia Terrace Rev SubDv. ⋅ 34236 Zip Code
Zoned for Short-Term Rental. This property is located in the high-demand Downtown Sarasota Perimeter, offering the perfect balance of urban energy and residential peace. This five-unit multi-family building is a rare find, featuring four efficient one-bedroom units and a premier two-bedroom unit with a versatile den. Plenty of room to add amenities and/or an elevator. Close to Downtown, restaurants, performing arts, Bayside Park, the Marina at Bayfront Park, The Bay County Park and our beautiful Sarasota and Manatee County beaches.

1236 13th Street, Sarasota
$1,525,000
4 Beds ⋅ 3 Baths ⋅ Owen Burns Sub SubDv. ⋅ 34236 Zip Code
Located in the dynamic Rosemary District, 420 Kumquat Court presents a compelling opportunity for investors and developers seeking position and flexibility in a downtown growth corridor. The property includes an existing triplex generating more than $5,000 per month in potential rental income, offering immediate cash flow while future development plans are evaluated. Zoned Downtown Edge (DTE), the site allows for residential, commercial or mixed-use development. The property is adjacent to Villa Ballada, a newly constructed five-story mixed use condominium featuring 24 residences, reinforcing the area’s continued investment and redevelopment momentum. An additional opportunity exists with the neighboring parcel to the south currently available. With a combined acquisition cost of $3,220,000, this option presents the potential for increased density, with the possibility to develop up to 24 residential units, subject to municipal approvals. The seller can also transfer plans for a seven-unit condominium project designed by award-winning Halflants + Pichette, providing a ready framework for development. Positioned within approximately six blocks of more than 60 restaurants, Sarasota Farmers Market, Sarasota Bayfront, Whole Foods Market and Sarasota’s arts and theater district, the location supports strong walkability and long-term demand. The Bay Park, a 53-acre waterfront park, is approximately four blocks away, with additional access to Payne Park and Legacy Trail. Connectivity is enhanced by the Bay Runner Trolley, offering service from downtown to St. Armands Circle and Lido Beach. This offering combines current income with future development potential in one of Sarasota’s most active urban districts.

420 Kumquat Court, Sarasota
$1,450,000
10 Beds ⋅ 5 Baths ⋅ Grove Park SubDv. ⋅ 34231 Zip Code
LOCATION LOCATION LOCATION! Sarasota's hottest zip code is Presenting a strong multifamily investment opportunity just minutes from Siesta Key, this 5-unit hotel/ motel property offers current income, flexible rental options, and long-term upside in one of Sarasota’s most desirable rental markets. Located in a non-flood zone approximately 4 miles from Siesta Key Beach, the property is well positioned for long-term tenants, seasonal rentals, or potential short-term rental strategies. The building includes five 2-bedroom, 1-bath units, each offering broad tenant appeal and turnkey convenience. Long-term tenants are currently in place, while the property has the availability to hold a motel/hotel license, creating additional flexibility for future ownership and rental operations. Investor-friendly features include individually metered utilities, public water and sewer, paved parking, no required flood insurance, and reported general liability insurance of approximately $460. Recent improvements include exterior paint in 2024, remodeled kitchens in Units 2, 3, and 4 in 2024, updated bathrooms, major plumbing replacement completed in 2009 and 2010, roof replacement in 2014, blown-in roof insulation. The property also offers private amenities that help set it apart from typical multifamily options, including a heated and cooled swimming pool, screened patio room, and tropical outdoor space designed to enhance tenant or guest enjoyment. With current income, multiple rental strategy options, turnkey units, and a prime Sarasota location near Siesta Key, this property is a compelling opportunity for investors seeking cash flow, flexibility, and long-term appreciation potential. Schedule your private showing today.

4001 Groveland Avenue, Sarasota
$1,300,000
4 Baths ⋅ Pelican Gardens SubDv. ⋅ 34236 Zip Code
Rare Income-Producing Portfolio on South Lido Key – 4 Turnkey STR Units A rare opportunity to acquire a fully operating short-term rental portfolio on South Lido Key, one of Sarasota’s most coveted coastal markets. This offering includes 4 updated studio units within a boutique beachside community just steps from two direct beach access points and a short ride to St. Armands Circle. Each unit is managed, actively listed, and consistently booked, delivering proven performance and strong guest demand year-round. These condos have a long track record as successful Airbnb rentals, with 2024 gross income averaging $38,470 per unit and portfolio-wide net income of $85804 after HOA, taxes, utilities, and cleaning expenses. This is a cash-flowing, turnkey asset in a high-barrier-to-entry vacation rental market. The property features a community pool and sliding glass access private patios for each unit, creating the indoor/outdoor lifestyle guests expect on Lido. Interiors have been updated over the years and show pride of ownership throughout. Major mechanical systems are in good condition, with recent A/C and hot water tank replacements across the portfolio for peace of mind. Unit Renovation & Mechanical Summary: • Unit 10 – Updated | AC ~2 yrs | WH < 6 yrs • Unit 11 – Updated | AC ~3 yrs | WH < 3 yrs • Unit 12 – Updated | AC ~2 yrs | WH < 3 yrs Unit 6 - Updated AC is 3 years and WH is 3 years This type of offering is rarely available — a multi-unit STR package on Lido Key with documented income history, repeat traveler base, and proven operational infrastructure already in place. Keep as a turnkey portfolio, self-manage, or explore value-add improvements and dynamic pricing to further enhance returns. 4 units. One unbeatable coastal investment. Opportunities like this do not come around often.

170 Roosevelt Drive Unit 10, Sarasota
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located approximately three blocks behind Siesta Key Village, the Hub of Restaurants, Nightlife, and Shops, and there you will find this Graceful Triplex and Cottage. There are several Private Patios as well as Open Areas for Outdoor Entertainment and Relaxation both in the Front and Rear of the Triplex. There are Storage Units for Each Rental and there is a Shared Laundry Area in the middle of the Backyard. Convenience is really key for this Property as you can Walk to the Beach or the Village in 15 Minutes. Island Life is Unique, Exciting, Colorful but can also be Quiet and Slow, it's the perspective of the Offering and it's a sought after way of living. For the past 20 years the units have been long term rentals. Some of the tenants have been there for years and all four would like to stay and continue their Florida Island Lifestyle. Rents shown are the Expected rents that could be charged as the Owner currently charges less... just his way of doing business. There is one option that could change the dynamics and that would be to keep the Triplex as long term rentals and use the rear Cottage as an AirBNB and Owners Use unit. This would drastically change the income stream. The water and internet/cable is currently paid for by the Owner and the Electric is split between the Tenants based on unit size, of course all of this is subject to change based on the New Owner's intentions. This is an Amazing Opportunity to have both Income and Personal Enjoyment all wrapped up with a Special Place we call Siesta Key Living!

618 Avenida De Mayo, Sarasota
$1,199,000
7 Beds ⋅ 7 Baths ⋅ Homecroft SubDv. ⋅ 34239 Zip Code
3 homes located in the HEART of PINECRAFT, A 4 bedroom, 3 1/2 bath MAIN HOME, a detached 2 BEDROOM, 2 BATH home and a 1 bedroom, 1 bath home...Use for INVESTMENT or a FAMILY COMPOUND... A renovation like no other by one of the best contractors in town. Both the MECHANICS and COSMETICS of these properties are astounding, with thought and consideration evident in every room. All the DRAINPIPES have been replaced with PVC, and the PRESSURE LINES are new and supported by TANKLESS HOT WATER HEATERS. The ELECTRICAL SYSTEM has been completely updated, including the panel, wiring, and fixtures. The NEW KITCHEN has stainless steel appliances and granite countertops, with an enormous number of cabinets and counter space. In the MAIN HOUSE, the primary bedroom is complemented by a spacious bathroom and walk-in closet, which includes an ADDITIONAL WASHER/DRYER for that end of the house. The OFFICE, located off the primary bedroom, has its own outside entrance. All the bathrooms are NEW, as are the IMPACT WINDOWS. The main house features a NEW METAL ROOF. The OUTSIDE KITCHEN is made of composite materials not prone to decay. Additionally, the property includes a DETACHED 2-bedroom, 2-bath home that has been completely renovated to the high standards of the owner/contractor, from the drainpipes to the new roof and has a 20 x 08 covered porch... There is also a DETACHED 1-bedroom, 1-bath apartment with a long-term tenant in place. The property boasts a HUGE GARAGE/WORKSHOP and a 2-car carport. Everything is connected by a spacious paver brick driveway and patio sitting area, surrounded by lush landscaping that brings the final touches to this TRULY REMARKABLE INVESTMENT or FAMILY COMPOUND

3502 Bahia Vista Street, Sarasota
$1,159,999
6 Beds ⋅ 5 Baths ⋅ Central Park SubDv. ⋅ 34236 Zip Code
FIVE UNIT APARTMENT COMPLEX. DTN zoned corner lot in downtown Sarasota. Fully rented month to month annual agreements paying below market value. City zoning allows weekly rentals. Purchase and earn rental income OR develop in DTN zoning. Common area laundry as an amenity for tenants. Bldg #1 has 2 units, each are 1 bedroom/1 bath. Bldg 2 has 2 units, each are 2 bedroom/1 bath. Bldg #3 is the cottage/studio. This property is in fast growing downtown Sarasota a few blocks to Main Street with downtown restaurants, shops and bars. 2 blocks from Sarasota City park with tennis courts, playground and dog park all situated around a lake! Many multimillion dollar homes and deluxe condo developments in and surrounding Gillespie Park. Close to beaches and beautiful Sarasota Bay. Investment property with huge income potential and huge future DTN development. Seller is offering owner/seller financing to prospective buyers. 60% minimum down payment requirement. All financing terms are extremely attractive. Minimum balloon options will be considered. Seller will not go into 2nd position as lender.

503 N Osprey Avenue, Sarasota
$1,099,000
4 Beds ⋅ 4 Baths ⋅ Towles Sub SubDv. ⋅ 34236 Zip Code
Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.

301 S Osprey Avenue, Sarasota
$1,050,000
6 Beds ⋅ 5 Baths ⋅ Sarasota Springs SubDv. ⋅ 34231 Zip Code
Being sold with the adjacent single-family home (MLS#A4682693) 3 UNITS TOTAL for $1,550,000 Welcome to Gone Coastal Villas, a rare three-unit coastal retreat just minutes from world-famous Siesta Key Beach in Sarasota. This exceptional property offers the perfect blend of personal enjoyment and income potential, ideal as a family compound, investment property, or both. Comfortably accommodating up to 12 guests, it’s perfectly suited for large gatherings or three separate vacation groups. The duplex features two mirrored two-bedroom, two-bath residences, each with private driveways, one-car garages, laundry, and storage. The beautifully updated Flamingo and Coastal cottages showcase open floor plans, vaulted ceilings, screened patios with grilling areas, and private above-ground spas. Adjacent is the Seashell Cottage, a charming single-family two-bedroom, one-bath home with a refined coastal contemporary design. All three turnkey furnished residences have been thoughtfully updated with cohesive coastal contemporary finishes. The shared courtyard offers an inviting outdoor experience with astro turf, a heated saltwater pool with sun shelf, gated vinyl fencing, lighted pathways, epoxy walkways, and paver driveways. Major improvements include new roofs (2017), on-demand hot water systems in all units, and newer HVAC systems. Located within one mile of shopping, dining, and entertainment, Gone Coastal Villas is truly move-in ready and positioned for immediate income with no upfront improvements required. Being sold with the adjacent single-family home (MLS#A4682693).

2051 Roselawn Street, Sarasota
$1,000,000
South Highland SubDv. ⋅ 34231 Zip Code
This beautiful rental property is located in the middle of Sarasota off Tamiami Trail. Walking distance to shopping and great restaurants. Close to Siesta Beach as well. The property is zoned RSF3. Monthly rental, each two bedroom , 2 bath unit epitomizes coastal living at its best. The attention to detail is everywhere. All the conveniences are included with this turnkey investment property. Beautiful outside area to relax in. Completely fenced in back yard oasis, independent from each side. The photos lend a view of this beautiful property, but go look at it you will immediately realize there is more to this great space. Located on the end of the street with no thru traffic makes this a perfect get away.

1805 Ivanhoe Street, Sarasota
$990,000
6 Beds ⋅ 6 Baths ⋅ Montclair Villas SubDv. ⋅ 34231 Zip Code
Montclair Villas offers a rare opportunity to own a 2007 masonry construction duplex in the Coquina Island area, just minutes from Siesta Key. The property features two spacious, two-story 3-bedroom / 2.5-bathroom units, each with an open living area, tile flooring, sliding glass doors, recessed lighting, decorative tray ceiling with crown molding, private swimming pool, screened patio, private yard, and two-car garage. Each unit also includes spacious bedrooms with decorative tray ceilings, crown molding, recessed lighting, and ceiling fans. All utilities are separately metered and paid directly by tenants, helping reduce owner-paid expenses. Additionally, each unit and the common area have separate parcel IDs, offering potential future flexibility through an individual condo sell-off strategy. Given its proximity to Siesta Key, the property may also be well-positioned for potential vacation rental use, providing multiple paths for future ownership flexibility. With quality construction, private outdoor amenities, garage parking, and a highly desirable location, Montclair Villas offers a compelling blend of residential appeal and long-term investment upside.

2119 & 2125 Montclair Drive Unit 1 & 2, Sarasota
$800,000
6 Beds ⋅ 4 Baths ⋅ Phillippi Gardens SubDv. ⋅ 34231 Zip Code
This nicely updated two-unit duplex in the desirable Phillippe Gardens community on Coquina Island offers excellent income potential in a highly sought-after location. Situated on a generous corner lot, each unit features 3 bedrooms and 2 bathrooms, including a private primary bath, along with a newer eat-in kitchen that flows seamlessly into the living room. UPDATES INCLUDE- 3 NEW BATHROOMS, NEW QUARTZ COUNTERTOPS, NEW FLOORS, NEW GARAGE DOORS. Both units include a private backyard, an attached garage, and the convenience of a large side drive with ample parking. The property is ideally located just 10 minutes from Siesta Key Beach, 12 minutes from Siesta Key Village, and less than 20 minutes from major shopping, downtown Sarasota, and top local attractions. With easy access to US-41, waterfront dining, vibrant nightlife, and award-winning Gulf beaches, this turn-key duplex is perfectly positioned for strong rental demand. Priced to sell, it presents a rare opportunity for investors seeking a ready-to-go property in an exceptional Sarasota location.

2227-2229 Montclair Drive Unit 1&2, Sarasota
$749,000
3 Beds ⋅ 3 Baths ⋅ Inwood Park SubDv. ⋅ 34236 Zip Code
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Live, invest, and work in the heart of downtown Sarasota. This beautifully renovated 1925 triplex is located in Gillespie Park and offers exceptional flexibility with short-term rentals allowed. Fully updated inside and out, the property presents a rare turnkey opportunity in one of Sarasota’s most desirable and walkable neighborhoods. The exterior has been meticulously improved with new landscaping, stylish pavers, artificial turf, a new privacy fence, updated roof, updated electric meters, energy-efficient windows and doors, and a modern sand-finish exterior. These upgrades provide strong curb appeal and long-term durability. All three units have been completely remodeled and are offered fully furnished. Renovations include new drywall, new subflooring, updated electrical systems, newer HVAC units, modern flooring, new kitchen cabinets, sleek appliances, updated bathroom vanities, toilets, showers, and fresh interior paint throughout. Each unit is move-in ready and designed for low maintenance and operational efficiency. The location offers unmatched convenience. Ideal for investors seeking strong income potential, or for an owner-occupant looking to live in one unit while renting the others. One or more photo(s) have been virtually staged.

1862 6th Street, Sarasota
$724,900
4 Beds ⋅ 4 Baths ⋅ Phillippi Park SubDv. ⋅ 34231 Zip Code
Great investment opportunity with strong income potential! This well-maintained duplex features two spacious units, each offering 2 bedrooms, 2 bathrooms, and a single-car garage, each on its own water and electric meter. One unit is being sold fully furnished and is ready for immediate rental, making it easy to start generating income right away. Both units have been remodeled and offer comfortable, inviting living spaces. The flexible layout makes this property ideal for a variety of investment strategies. Live in one unit while renting the other, lease both units for maximum income, or create the perfect multi-generational living setup. The choice is yours! Recent updates provide added peace of mind, including a roof installed in 2022 and updated AC units installed in 2022 and 2024. The property also weathered the recent storms with no damage, further highlighting its durability and care. Located just minutes from world-renowned beaches, including Siesta Key Beach, this property offers easy access to golf courses, shopping, dining, and the vibrant arts and cultural scene of Sarasota. Whether you're expanding your investment portfolio or searching for a property with income-producing potential and lifestyle appeal, this duplex presents a rare opportunity in a highly desirable location. Come see, come sigh and make this property your own!

2214 Michele Drive, Sarasota
$719,000
4 Beds ⋅ 4 Baths ⋅ Desoto Terrace SubDv. ⋅ 34234 Zip Code
NEW PRICE-Well-maintained, income-producing turn-key duplex located at 3710 & 3712 Iroquois Avenue in the established Sapphire Shores submarket of Sarasota. Each unit is configured with 2 bedrooms and 1 bath each 852 square feet, offering functional layouts with updated kitchens, remodeled baths, and efficient living and dining spaces that support consistent tenant demand. Interior renovations were completed in 2017, followed by substantial capital improvements in 2020, including new stucco, roof, windows, flooring, kitchens, and baths—reducing near-term capital exposure. Each unit operates independently with separate utilities and in-unit laundry, supporting operational efficiency and long-term tenancy. One A/C was replaced with new, in 2024. All furnishings convey, allowing for a turnkey transition and uninterrupted rental operations. The property demonstrates consistent occupancy and documented performance of both 2024 and 2025, each north of $70,000 gross, with forward bookings already in place for 2026. No HOA and no CDD provide added flexibility and help contain ongoing ownership costs. Operating expenses are tracked annually and available for review. Sapphire Shores remains a durable rental location due to its proximity to Downtown Sarasota, the Ringling Museum District, bayfront parks, and direct access to US-41, beaches, and major employment corridors. This asset offers a proven rental history, completed capital upgrades, and stable location fundamentals—well-suited for an investor prioritizing durability, efficiency, and long-term hold potential. Complete financials, operating history, available. Showing scheduled on the turnover days schedule, permitting.

3710 Iroquois Avenue, Sarasota
$679,777
2 Beds ⋅ 4 Baths ⋅ Shenandoah Park SubDv. ⋅ 34237 Zip Code
Rare opportunity for a Quadplex in Sarasota City limits and 2 blocks from Downtown now available with potential to purchase 620 N East Ave (2bd/1ba single family) next door for a combined .35acres! This quadplex features 2 block buildings, 2 studio units in one building at 610/612 East Ave and 2, 1 bedroom units in the other building at 2115/2117 6th St. Studio units are occupied while the 1 bedroom units are currently vacant and rent ready. See photos for current condition of all units. Walkthrough Video of units available upon request. Realtors please check showing details. Vacant units can be shown at anytime. Short-Term Rental, Property enhancements, and/or development opportunities await the next owner!

610 N East Avenue, Sarasota
$650,000
8 Beds ⋅ 8 Baths ⋅ Poinsettia Park SubDv. ⋅ 34239 Zip Code
Investor alert!! Grandfathered Duplex located West of the Trail in Poinsettia Park. You have a few options with this property. You can keep it as duplex and rent it out long term or short term because it's in the city limits. But please note the property needs work and it's prime for a remodel. Currently it's a 2 bedroom and two bath on each side. Alternatively tear it down and put up a single family home. The real value is in the dirt. Million dollar homes surround the property on every side.

1824 Webber Street, Sarasota
$649,000
3 Beds ⋅ 2 Baths ⋅ Indian Beach SubDv. ⋅ 34234 Zip Code
Come see this charming and peaceful Old Florida gem with detached cottage ideally situated in the desirable Indian Beach/Sapphire Shores neighborhood located west of the trail. Here is a rare opportunity to own two meticulously maintained homes within the city limits in Indian Beach/Sapphire Shores, a community rich with art, culture, and history. This property has been a high-yielding asset for the seller. The seller gets a high volume of applicants, and it has required minimal effort to lease. Picture tree-lined streets, character-filled homes, and being just moments from the shimmering Sarasota Bay. You are in for a treat as you enter the main home through a central air-conditioned enclosed front porch into a home with all of its original, timeless character including glass doorknobs, lovely baseboards and trim, vintage light fixtures, painted heart of pine floors, and functional double-hung windows. This original 1930s home (732 sf) features two bedrooms (freestanding wardrobes), one bath, and a spacious combination dining/living area. An additional wonderful highlight is the central air conditioned detached guest cottage (478 sf) with kitchen, living area, one bathroom and bedroom alcove along with a screened porch and patio, and attached one-car garage. This cottage is ideal for multi-generational living or Airbnb or full-time lease opportunities. All furnishings and fixtures convey: the front unit is partially furnished; the back unit is turn-key furnished. The property includes a very nice new 12x16 Tuff Shed ideal for an artist’s studio, workshop, or just additional storage. Set on a lush 12,000+ square foot lot, the property is spacious with plenty of room for parking, entertainment and other possibilities. You are sure to enjoy the established vegetable and flower gardens. Adding to the charm, you may catch sight of the neighborhood's colorful wild peacocks who love to display their feathers. Excellent location just minutes from the Ringling Museum, SRQ Airport, and downtown Sarasota as well as close proximity to Lido Key Beach, St. Armands Circle, and Siesta Key. Two high-end homes are currently under construction on the block. This sweet property is waiting to fit your needs whether as live-in residences, a rental investment, multi-generational living, or any combination thereof. This peaceful neighborhood in "Turks Cap" (sometimes referred to as the Museum District) has a rural feel with narrow, tree-lined streets and roaming peacocks. This is a no through street with no traffic. If you want quiet and relaxed, you have found the neighborhood.

708 42nd Street, Sarasota
$639,800
4 Beds ⋅ 2 Baths ⋅ Gillespie Park Sub SubDv. ⋅ 34236 Zip Code
Prime Sarasota DTN Zoning property. Discover this beautifully remodeled duplex ideally located just minutes from Lido Beach, St. Armands Circle, and downtown Sarasota. Each unit features 2 bedrooms and 1 bathroom, Newer Roof, Newer Air conditioners, offering bright, open living spaces with updated finishes throughout. The interiors have been tastefully remodeled, complemented by new windows that bring in plenty of natural light. Outside, enjoy a newly installed paver driveway providing great curb appeal and low-maintenance living. Perfect opportunity for an investor or owner-occupant looking for income potential in a prime Sarasota location.

721 N Osprey Avenue, Sarasota
$620,000
Ramblewood/Carolina Est Area SubDv. ⋅ 34237 Zip Code
Discover the potential of this multi-tribe property located at 1213 Benedict Ct, Sarasota, FL. This property accords a fantastic opportunity for those looking to invest in a versatile space. Situated in a convenient Sarasota location, this property is designed to accommodate multiple households, making it an superb choice for generating rental income or housing extended tribe members. The property is nestled in a neighborhood that provides easy access to local amenities, ensuring a comfortable and convenient lifestyle for its residents. With its strategic location in Sarasota, this multi-tribe residence accords a unique combination of privacy and community living. Whether you are an investor or seeking a home for multiple occupants, this property holds the promise of a rewarding real estate venture. Don't miss the chance to explore the possibilities that 1213 Benedict Ct has to accord.

1213 Benedict Court, Sarasota