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$524,900
3 Beds ⋅ 4 Baths ⋅ Marlowe Park SubDv. ⋅ 34234 Zip Code
Virtually Staged. Rare 4-unit multifamily income opportunity in Sarasota's North Trail corridor, just minutes from downtown Sarasota, the bayfront, and the Ringling College of Art & Design district. The offering pairs dependable in-place cash flow with real value-add and redevelopment upside on an oversized ~0.40-acre city lot (17,555 SF). Four income-producing units include three residences at 3917 (a 1BR/1BA plus two efficiencies) and a spacious 2BR-plus-bonus home at 3919, with the 3919 unit turning now and targeting a market lease. All units are currently month-to-month, giving a new owner full flexibility to raise rents to market or reposition on their own timeline, with no long-term leases to inherit and clear upside as rents step up. Recent ownership has reinvested in the major systems, lowering near-term capital exposure: the shared 3917 roof was replaced within the last five years, water heaters for the three 3917 units were updated in 2023, and Unit A carries a 2022 AC air handler, while 3919 adds a newer AC and water heater, a carport, and a paved patio. Located in the City of Sarasota's North Trail redevelopment overlay, the parcel offers long-term assemblage and development optionality in one of Southwest Florida's most supply-constrained infill pockets, backed by steady rental demand from the surrounding Ringling College submarket. Offered at $524,900

3917 Royal Palm Avenue, Sarasota
$499,000
3 Beds ⋅ 3 Baths ⋅ Las Lomas De Sarasota SubDv. ⋅ 34231 Zip Code
Live in One, rent the Other. A rare opportunity to own a primary residence with the ability to generate supplemental rental income. *Sold fully furnished and turnkey.* This newer construction corner lot residence provides reliability as well as a smart income play: a 2-bedroom, 2-bath main residence paired with a fully separate 1-bed, 1-bath studio with its own private entrance, kitchenette, and bathroom enabling the tenant to be completely independent. With recorded revenue of over $12,000 annually for the studio, you will experience real cash flow to help offset your mortgage from day one where affordable living is at high demand. The open-concept, split floor plan in the main house features in-house laundry, a primary suite with walk-in closet and ensuite, plus a 2-car garage for storage. This home is situated in a prime location just 10 minutes to downtown Sarasota and Siesta Key. It is also located within Sarasota County's top school district and local hospitals. Built to modern code with impact-rated windows, updated plumbing, and updated electrical systems, this home offers the peace of mind of newer construction with no aging infrastructure, no surprise repairs, just reliable, low-maintenance living from day one. Here you can live comfortably and rent confidently — this is smart living at its finest.

2011 Outer Drive, 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
$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
$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
$460,000
4 Beds ⋅ 2 Baths ⋅ Harriet Sub SubDv. ⋅ 34234 Zip Code
Lender incentive available for qualified borrowers on primary residents only. Exceptional income-producing duplex located within the Sarasota city limits in desirable Flood Zone X, meaning no flood insurance is required. This solid block construction property offers multiple investment opportunities including owner-occupancy, short-term rentals, long-term rentals, student housing, or a hybrid income strategy. Located directly across from the revitalized North Water Tower Park, residents and guests can enjoy paved walking trails, a disc golf course, playground, covered picnic areas, public restrooms, and a water bottle filling station. Each private unit features 2 bedrooms and 1 bathroom with beautifully updated kitchens showcasing shaker cabinetry, quartz countertops, timeless restored terrazzo flooring, open-concept living areas, private laundry rooms, screened lanais, and covered carports with locked storage. Unlike many duplexes, the units do not share a common wall or yard space, offering enhanced privacy and reduced noise between occupants. Major capital improvements have already been completed within the past seven years, including the roof, dual HVAC systems, and water heaters. Additional investor-friendly features include separate utilities and durable block construction. The property’s central location provides quick access to Downtown Sarasota, Bradenton, Lakewood Ranch, SRQ Airport, Ringling College, New College, University of South Florida, and world-famous Gulf beaches, supporting a strong tenant and guest pipeline with future rental growth potential. According to the City of Sarasota permitting website, the occupancy use is listed as R1 Hotels/Motels/Boarding House, creating flexibility for multiple income-producing uses. Unit B has been operating as a short-term rental through Airbnb and VRBO since January 2026 and has already generated approximately $13,926 in rental revenue. Unit A is currently owner-occupied. The current owners originally purchased the property using FHA financing as their primary residence, demonstrating an excellent opportunity for buyers interested in “house hacking” by living in one unit while offsetting expenses with rental income from the other. With three major colleges nearby, the property also presents excellent potential for student housing demand. Whether you are an investor seeking cash flow, a buyer looking to offset monthly expenses through owner-occupancy, or someone searching for a flexible income-producing property in a rapidly growing Sarasota location, this duplex offers outstanding versatility and long-term upside potential.

993 Gary Street Unit A & B, Sarasota
$429,000
5 Beds ⋅ 2 Baths ⋅ Newtown SubDv. ⋅ 34234 Zip Code
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.

1610 22nd Street, 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
$1,050,000
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
$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
$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
$525,000
4 Beds ⋅ 2 Baths ⋅ Walpoles Sub SubDv. ⋅ 34237 Zip Code
Investment opportunity, a corner lot duplex, located between downtown and Ringling College. Each unit has 725 sq ft with 2 bedrooms, 1 bath and the convenience of an attached carport. New Roof in 2025, Re-pipe, roof 2011. Each unit has a fenced in yard, Mango and Avocado trees in one side. Tenants are currently in place on a month to month. Being sold As Is. Please do not disturb tenants. A great investment in an unbeatable location, with all of the amenities of downtown Sarasota, local colleges, St Armands Circle, and beaches near by.

2100 9th Street, Sarasota
$1,129,000
4 Beds ⋅ 4 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code
Rare Beach-Area Duplex Just a 7-Minute Walk to Nokomis Beach! This beautifully remodeled, income-producing duplex offers the perfect combination of coastal living, flexibility, and investment potential. Whether you're looking for a live-in-one, rent-the-other opportunity, a multi-generational property, a family compound, a seasonal retreat, or an investment property with immediate income potential, this rare offering checks all the boxes. Located at 312 Bayshore Drive, this turnkey duplex features two beautifully updated residences with nearly identical floor plans, each thoughtfully remodeled with relaxed Florida coastal style. The property is ideal for retirees seeking supplemental rental income, first-time buyers wanting help with their mortgage, investors looking for a turnkey rental property, or families wanting private space for parents, adult children, or visiting guests. Step outside to your own private tropical retreat featuring an expansive patio and a resort-style heated pool measuring approximately 35' x 16'. New pool equipment and an automated lighting system create beautiful evening ambiance while providing effortless year-round enjoyment. Major improvements provide exceptional peace of mind and long-term value, including hurricane impact windows, a newer roof, newer A/C systems, newer A/C units for both bonus rooms, newer septic system and drain field, and newer pool equipment. Even better, this property has never experienced flooding or storm damage—a rare and valuable feature this close to the Gulf. Each residence includes its own bonus room with air conditioning and television, attached to the garage structure, offering flexible space for a home office, hobby room, fitness room, guest space, or additional living area. Designated parking is provided for each unit. Enjoy an unbeatable location just minutes from the Venice Jetty, Jetty Park, Nokomis Beach, a nearby marina with boat and jet ski rentals, waterfront dining, Pelican Alley, Pop's Sunset Grill, and the charming shops and restaurants along Venice Avenue. With two separate residences, exceptional updates, beach proximity, and immediate rental potential, this property offers countless possibilities: owner-occupy one unit while generating income from the other, accommodate extended family with privacy, create a seasonal snowbird retreat, or continue operating it as a turnkey income-producing investment. Opportunities like this are rare. Beach-area duplexes with this level of renovation, flexibility, and income potential don't come along often.

312 Bayshore Road, Nokomis
$550,000
4 Beds ⋅ 4 Baths ⋅ Walkers Sub SubDv. ⋅ 34236 Zip Code
A compelling investment opportunity within Sarasota city limits and only one mile from Downtown. This side by side duplex features two matching 2 bedroom, 1.5 bath townhome style units that have been updated to attract quality tenants and support strong rental performance. Being located inside the city limits also allows weekly rentals if desired, giving investors valuable flexibility in their strategy. Each unit offers bright, modern interiors with durable tile flooring on the main level, upgraded kitchens with shaker cabinetry, stainless appliances, contemporary backsplash details, and clean finishes that keep future maintenance simple and predictable. The upstairs layout includes two comfortable bedrooms and a full bath, creating an efficient and easy to lease floor plan that works well for both long term and short term tenants. Both 1610 and 1612 enjoy fully fenced private backyards with one featuring a spacious grassy area with a dedicated patio setting, while the other includes a relaxed fire pit lounge framed by mature Florida trees. This separation gives each unit its own appeal and enhances the property’s overall appeal. Parking directly in front of each entrance adds another convenience tenants appreciate and owners benefit from. With no association fees, modern updates, low maintenance features, and strong demand in the surrounding area, this duplex performs well as a straightforward income producing asset. Investors can maximize returns across both units, while those seeking flexibility have the option to live on one side and lease the other. A turn key opportunity in a highly desirable location near parks, cultural venues, Sarasota’s waterfront, and the downtown core. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

1610 & 1612 N Orange 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
$299,000
2 Beds ⋅ 4 Baths ⋅ Tyler & Darlings SubDv. ⋅ 34223 Zip Code
Motivated Seller! Less than three miles from the beach, this property is in the X flood zone and offers both a welcoming main home and a detached 320-square-foot efficiency apartment, making it the perfect setup for a family home with added income potential. Live in the main residence and rent out the guest cottage, or keep it for visiting family and friends. Outside you will find low-maintenance xeriscaping, a brand new garage door, and privacy fencing. Step inside the main home where there is easy care tile flooring throughout the main living areas and a kitchen with granite countertops, soft-close wood cabinetry, and plenty of storage. A cozy dinette sits just off the kitchen with sliding glass doors to the screened lanai, letting you open the home and enjoy salty coastal breezes flowing through the home. Both bedrooms have reach-in closets, while the shared bathroom has been updated with a granite vanity and a shower-tub combination. In the single-car garage there is a laundry area and a convenient half bath. The backyard is designed for outdoor living, complete with an oak shade tree, privacy hedge along the lanai, and a paver patio that’s ready for entertaining or quiet evenings outside. The detached efficiency cottage is a wonderful bonus. With tongue-and-groove ceilings that add warmth and character, this open layout combines living, dining, sleeping, and a kitchenette into one versatile space. A walk-in shower and single-sink vanity finish out the bathroom, making it ideal for generating rental income, creating a personal retreat, or accommodating multi-generational living. Located close to everything in Englewood you will be able to easily enjoy the weekly Farmer’s Market on Dearborn, listen to live music at one of the several tiki bars and restaurants after a trip to the beach, take in a ballgame at one of the two major league Spring Training Facilities, visit one of the many nature parks or hike the trails for exercise. No matter what you enjoy, you will find everything within close proximity. Venice Beach and Downtown is less than 15 miles away and Port Charlotte is less than 17 miles away, you will be right in the middle of all the hub and activity of the area, yet enjoy the privacy and small town charm Englewood provides. Here, you’ll enjoy the privacy and small-town charm of Englewood with the convenience of nearby cities and attractions. This home with a guest cottage located at 25 1st Avenue truly combines lifestyle and opportunity. Schedule your showing today and see for yourself everything it has to offer.

25 1st Avenue, Englewood