Investment Properties

A rare, one of a kind Sarasota investment opportunity offering incredible flexibility, privacy, and income potential! Come invest in one of the most highly desirable areas in Florida. 1 parcel features 3 detached single family homes, plus additional space with potential to build a fourth home. Each residence offers 3 bedrooms and 2 bathrooms with updated interiors, charming individual designs, and lush tropical landscaping throughout. At the heart of the property is an inviting shared pool area with cabana spaces, creating a private tropical setting to relax, entertain, and enjoy the Florida lifestyle. The property is extremely private, with lush surroundings and plenty of room to expand and create an even more impressive compound. Currently income producing, the property includes active vacation rentals, while one cottage is utilized as student housing with bedrooms rented individually. Its proximity to Ringling College of Art and Design and New College of Florida adds another layer of rental potential. Continue the existing strategy or reimagine the property as a multi generational retreat, artist compound, private residential compound, or a unique setup for friends who want to live close while maintaining their own private residences. Tucked away on a private dead end street with no HOA and outside of a designated flood zone, the location is exceptional. Minutes from Downtown Sarasota, The Ringling Museum, Sarasota Bradenton International Airport, Ringling College, New College, dining, shopping, and Sarasota Bay, which is even within walking distance. With 3 existing homes, a pool and cabana area, multiple income possibilities, exceptional privacy, and room for future expansion, opportunities like this are incredibly hard to find in Sarasota. Keep everything operating as is and generate income, or bring your vision and unlock even more potential. Book your private showing today before your next investment opportunity in Sarasota,Florida is gone!

3476 Winton Avenue, North Sarasota

$1,750,000

3 Beds ⋅ 3 Baths ⋅ A4705510 MLS

Island living meets proven vacation-rental performance in this beautifully maintained Holmes Beach home! Whether you’re searching for your own Anna Maria Island retreat or an established income-producing property, this home offers the rare combination of tropical privacy, generous indoor and outdoor living space, and an impressive history as a successful vacation rental. Currently licensed for short-term rental use with the City of Holmes Beach, the property allows a minimum 7-night stay and comes with something particularly valuable to an investor: an established rental history, repeat clientele and bookings already extending into 2027. The home has earned an exceptional 10/10 rating on VRBO from 163 guest reviews, with guests repeatedly praising the pool and spa, cleanliness, comfortable accommodations, well-stocked home and easy walk to the beach. Some returning guests have vacationed here for nine years—and have already booked again for 2027. The home itself was made for the Florida lifestyle. Bright, comfortable living spaces flow easily into multiple outdoor areas, while the lush tropical surroundings create a wonderful sense of privacy. The expansive covered lanai provides an incredible amount of room for dining, entertaining and relaxing out of the Florida sun, while the upper covered balcony offers another peaceful spot surrounded by palms. At the heart of the outdoor experience is the private saltwater pool and spa, beautifully tucked into the tropical landscape and featuring a specially designed non-slip surface. The pool has been exceptionally well maintained, with a new heater installed in October 2024 and additional equipment updates and a comprehensive maintenance review completed in 2026. Remote Pentair ScreenLogic controls allow the pool and spa to be managed from virtually anywhere. Inside, the spacious kitchen offers abundant cabinetry and counter space and opens to the main gathering areas which boasts twelve foot high ceilings, enhancing the feeling of space and light in the dining and living areas. The primary suite includes a generous bath with dual vanities, soaking tub and separate walk-in shower, while additional bedrooms provide comfortable accommodations for family and guests. Thoughtful ownership is evident throughout, including two modern and meticulously maintained HVAC systems, with the main-level Lennox installed in 2022 and the upper-level Trane installed in 2018, along with numerous recent appliance, mechanical and equipment updates. Remote thermostat access makes managing the property especially convenient for an owner who may not live locally. The property also holds a current Holmes Beach Rental Certificate valid through May 2028 and successfully completed its 2026 West Manatee Fire & Rescue inspection. HOA fees include several significant ownership expenses, including flood and property/casualty insurance, grounds maintenance, trash removal, pest and termite treatment, exterior maintenance, irrigation and backflow testing. Come for the island lifestyle—or step into a turnkey furnished vacation property with a track record already in place. Either way, this is a home designed to make the most of life on Anna Maria Island.

310 63rd St, Bradenton Beach

$599,900

5 Beds ⋅ 3 Baths ⋅ TB8543902 MLS

Investor & Multi-Generational Focus (Income Potential) Dual Income Opportunity / In-Law Suite on an Oversized Double Lot! Don't miss out on 4500 3rd Ave S in St. Petersburg! This turn-key investment or multi-generational property sits on an impressive double lot with two distinct living spaces. Main House: Spacious 4 Bedrooms | 2 Bathrooms | Attached 1-Car Garage ADU (Built 2019): Modern 1 Bedroom | 1 Bathroom detached secondary residence Key Features:BRAND-NEW ROOF scheduled for installation on the main house by the end of September! Independent Privacy: Both the main home and the ADU feature their own fully fenced private yards. Prime St. Pete Location: Easy access to downtown, Tampa Bay, and the Gulf beaches. Whether you're looking to house hack and live in one unit while renting the other, generate dual rental income streams, or set up a multi-generational living quarters, this property checks every box!

4500 3rd Avenue S, Gulfport

$395,000

4 Beds ⋅ 4 Baths ⋅ C7530468 MLS

Harbour Heights in Punta Gorda! This duplex features two self-contained units each with 2 bedrooms and 2 baths. Great income opportunity to live in one unit and rent out the other or use it for guests or in-laws. The two units are connected by a common wall, but each has its own entrance, kitchen, bathrooms, and bedrooms, creating a sense of privacy and independence for each resident. Both units are open and spacious with high ceilings, new fixtures, recessed lighting, and quality vinyl flooring. Both kitchens have granite countertops, hardwood cabinets, loads of storage, and stainless appliances. Outside features a private covered patio, perfect for grilling or enjoying your evening outside. Each unit has its own long driveway with plenty of parking spaces. This duplex is nice as it provides an income for you. Rent one or both sides in this low maintenance, HOA FREE zone. Harbor Heights Park is close by with public boat ramp, fishing piers, basketball, tennis, pickleball, picnic tables, playground plus much more! Great location close to restaurants, shopping, schools and downtown historic Punta Gorda with world-class fishing and boating, beautiful parks, community events and entertainment. Don’t miss this opportunity!

27233 Partin Drive, Punta Gorda

$2,350,000

6 Beds ⋅ 6 Baths ⋅ TB8546917 MLS

Construction just completed !New duplex located steps from beach and vibrant IRB. Spacious two-car garage on the first floor can accomodate golf carts, surfboards, and more. The second floor offers an open living space composed of kitchen, quartz countertops, a living area, and a half bath. On the third floor three bedrooms and two full bathrooms, ideal for family and guests. On the fourth floor, beautiful partial views of the Gulf of America , to relax, and enjoy with family and friends. Short distance from Splash Harbour Water Park, restaurants, cafés, and other attractions, don't miss this magnificent new duplex. There is an easement to allow access to all garages for both buildings (709 and 711 Gulf Blvd) Next door duplex also for sale . Listing T88506388.

709 Gulf Boulevard, Belleair Beach

$575,000

4 Beds ⋅ 3 Baths ⋅ O6440485 MLS

Rare full duplex opportunity in College Park, just 0.9 miles from Edgewater Drive, 2.5 miles from Downtown Orlando, and 3.5 miles from Park Avenue in Winter Park. The property has generated approximately $60,000 in average annual gross revenue from mid-term rentals and has maintained a 5-star Airbnb rating. Both units feature large closets, washers and dryers, and freshly painted interiors. Recent improvements include updated electrical, plumbing, water heater, newer AC, bathroom vanities, refrigerator, and a kitchen island. Existing furnishings may potentially be included with the sale, making this a strong opportunity for an investor or owner-occupant seeking income potential in a central Orlando location.

46 E Princeton Street, Orlando

$325,000

4 Beds ⋅ 2 Baths ⋅ O6439738 MLS

INCOME-PRODUCING DUPLEX – FULLY REMODELED with WASHER & DRYER HOOKUPS in EACH UNIT!! Minutes from DOWNTOWN OCALA! ROOF (2023), NEW WINDOWS (2024), NEW AC (2024), and 2 BACKYARDS. One side is currently tenant occupied, with the tenant renewing for another 12-month term beginning in October. The right side recently had a tenant move out. Live in one side while income from the other helps offset your housing expenses, or lease both residences and expand your investment portfolio. Each residence features 2 beds, 1 bath, and 744 square feet. GRANITE COUNTERTOPS, updated cabinetry, glass-tile backsplashes, stainless steel appliances, recessed lighting, tile flooring throughout, beautifully updated bathrooms, and dedicated washer and dryer connections. Outside, each residence enjoys its own separate backyard, providing valuable private outdoor space across the generous .28-acre lot. .Located near Downtown Ocala, Tuscawilla Park, the Reilly Arts Center, shopping, dining, and public transportation, this updated duplex offers rental income already in place and additional income potential from day one. A covered front patio, NO HOA, PUBLIC WATER, and PUBLIC SEWER add even more convenience. Located near Downtown Ocala, Tuscawilla Park, the Reilly Arts Center, shopping, dining, and public transportation, this updated duplex offers rental income already in place and additional income potential from day one.

1135 Ne 9th Avenue, Ocala

$270,000

3 Beds ⋅ 2 Baths ⋅ TB8545113 MLS

Welcome to this well-maintained duplex in the heart of Zephyrhills, offering an excellent opportunity for both homeowners and investors. The front unit features a 1-bedroom, 1-bath layout with approximately 385 sq ft—ideal for rental income, guests, or multi-generational living. The property is move-in ready and has been thoughtfully maintained, featuring a newer roof, newer flooring and a water heater just a few years old. Additional features include a dedicated laundry room, storage area, screened-in porch and a large fenced yard with rear alley access—perfect for added convenience and privacy. Ideally located near Zephyr Park, Skydive City, and major routes including US-301, this property offers easy access to Wesley Chapel, downtown Zephyrhills, and Tampa for shopping, dining, and entertainment. Whether you’re looking for a primary residence with income potential or a solid investment property in a growing area, this duplex checks all the boxes.

4920 17th Street, Zephyrhills

$1,400,000

4 Beds ⋅ 4 Baths ⋅ FC321313 MLS

Four income streams, one block from the beach, directly across from the new Compass Hotel by Margaritaville. This fully renovated four-unit mixed-use building sits on a rare double lot in the heart of downtown Flagler Beach — zoned Mixed Use General Commercial, which permits short-term rentals, long-term rentals and commercial tenants. In a city where new short-term rental registrations are limited that entitlement is close to impossible to reproduce. The two upper units are leased to long-term tenants on annual leases, producing income from day one. Both ground-floor units are delivered vacant, so you set the rents: one is a finished residential apartment, the other a true turnkey storefront with a full ADA bathroom, handicap parking space and ramp — ready for a boutique, studio, café, gallery, bakery or office. Every unit has been renovated within the last five years: new LVP flooring, new kitchen cabinets and countertops, updated bathrooms, new water heater and a new roof. Outside is where this property separates itself. Five dedicated parking spaces plus side-street public parking. A fully fenced backyard with an oversized paver patio and fire pit — an exceptional shared amenity for commercial tenants or a private retreat for guests. Rear alley access for deliveries and service. And the city has approved a secondary building on the lot, opening the door to additional units and materially higher revenue. The location is doing the work for you. You are two blocks from the sand, steps from downtown's shops and restaurants, and next door to the rebuilt Flagler Beach Pier — an $18 million replacement due to reopen and return foot traffic to the center of town. Live in one and let the other three pay for it. Add a boutique short-term rental. Lease the storefront and build out the back lot. This is the flexibility a single-family beach house cannot offer, on the last kind of downtown lot Flagler Beach still has.

212 S Daytona Avenue, Flagler Beach

$2,495,000

8 Beds ⋅ 8 Baths ⋅ TB8546389 MLS

Exceptional investment opportunity in the heart of highly desirable Hyde Park. 509 S Willow Avenue offers a rare and versatile property consisting of two spacious 4-bedroom, 3.5-bath residences, each configured as a 3-bedroom, 2.5-bath main townhouse with an additional approximately 500-square-foot 1-bedroom, 1-bath rear apartment. Each residence offers approximately 2,800 square feet of main living area and an oversized 2-car garage. Quality construction and finishes are found throughout, including 12-foot ceilings on both floors, crown molding, travertine flooring throughout the main living areas, granite countertops, stainless steel appliances, raised-panel cabinetry and solid wood doors. Andersen double-pane windows and patio doors, masonry construction and numerous additional structural upgrades further distinguish these residences. The commercial-grade TPO roof was replaced in 2017, and the owner carries a 20-year warranty through December 2037 that may be transferable for a $500 fee. Additional property and construction information is available upon request. The property is currently leased and operated by a professional short-term rental management company, with an established rental history and reservations extending into 2027. Rental history and financial performance information are available to qualified buyers upon request. For buyers interested in continuing the property's current use, the existing management company is willing to continue professionally managing the short-term rental operation. offering the potential for a seamless transition following closing. Continuation or transfer of existing reservations is subject to applicable agreements and arrangements between the parties. The property is currently fully furnished and equipped for short-term rental use. Furnishings, electronics, fitness/gym equipment and other operational items are not included in the real estate offering price but may be available for purchase separately, creating the potential for a turnkey acquisition. The flexible configuration offers numerous possibilities, including short-term or long-term rental use, multigenerational living, guest accommodations or owner occupancy, subject to applicable regulations and restrictions. Ideally located near Hyde Park Village, Bayshore Boulevard, SoHo, Downtown Tampa and the University of Tampa, with convenient access to dining, shopping, entertainment and recreation. A distinctive opportunity to acquire two substantial residences with additional private living spaces in one of Tampa's most desirable neighborhoods. Property is actively operated as a short-term rental and may be occupied by guests. Showings are by appointment only and must be coordinated with the listing agent. Please do not disturb occupants.

509 S Willow Avenue Unit 1 & 2, Tampa

$439,000

4 Beds ⋅ 4 Baths ⋅ R4911947 MLS

Prime investment opportunity in Lake Alfred! Built in 2023, this modern, turn-key duplex delivers instant cash flow with tenants already in place. Sitting on a ~0.17-acre lot with a private, fully fenced yard and NO HOA, this property offers ultimate flexibility for hands-off landlords or house-hackers looking to live in one side and offset their mortgage. Both units boast a functional, open-concept 2-bedroom, 2-bathroom layout finished with fresh paint, durable low-maintenance flooring, and upgraded stainless steel appliances. Positioned right in the heart of town, residents enjoy fast access to US-17/92 and I-4 for effortless commutes to Orlando or Tampa, along with close proximity to local lakes, the Chain of Lakes Trail, and a planned Publix-anchored development. Portfolio Opportunity: Motivated seller! Can be acquired individually or bundled with the matching, 1,800 sq ft duplex right next door at 640 E Grapefruit Ave (Parcel: 26-27-28-493500-00130) for a target 6.24% portfolio cap rate. Multiple financing options available—schedule your private tour today! Disclaimer: Photos depict the vacant unit. Floor plans, interior finishes, and color schemes may vary slightly by unit.

650 E Grapefruit Avenue, Lake Alfred

$1,500,000

6 Beds ⋅ 6 Baths ⋅ PR9123958 MLS

1364 Calle Estrella: Prime Investment Opportunity in the Heart of San Juan Located in one of San Juan’s most vibrant neighborhoods, this exceptional 2,500sqft property at 1364 Calle Estrella offers the perfect blend of relaxation and urban culture. Situated on a peaceful residential street in Condado, the property is steps away from the culinary hub of La Placita de Santurce and minutes from Condado pristine beaches. The property has been recently remodeled and redesigned into five independent units, all featuring fully updated electrical and plumbing systems: • Unit 1 (1st Floor): 1 Bed / 1 Bath, 450 sqft. Includes 2 AC units and a full kitchen. • Unit 2 (1st Floor): 2 Bed / 1 Bath, 600 sqft. Includes 3 AC units, a full kitchen, and a small balcony. • Unit 3 (2nd Floor): 3 Bed / 2 Bath, 1,100 sqft. Includes 4 AC units, a full kitchen, washer/dryer, and exclusive use of the parking space. • Unit 4 (2nd Floor): Studio, 250 sqft. Includes 1 Bath, 1 AC unit, and an integrated kitchen. • Unit 5 (1st Floor): Studio, 250 sqft. Includes 1 Bath, 1 AC unit, and an integrated kitchen with induction cooktop. The property is designed for efficiency and convenience, featuring: • A new Caterpillar diesel backup generator. • A 1,000-gallon water system cistern. • New gas connections for all units and the water heater. • High-speed internet. Whether for high-profit Short-Term Rental (STR) or Long-Term Rental (LTR), multi-generational living, this property offers excellent passive income potential. Its strategic location is highly desirable to professionals and tourists alike. Residents enjoy easy access in Condado, to local fresh produce markets, and the premier nightlife zone. The property also provides convenient access to main avenues, the Expressway, Hayo Rey Financial District, Historic Old San Juan, and the Luis Muñoz Marín International Airport (SJU). Offered “As-is”, fully furnished and equipped.

1364 Estrella, San Juan

$1,295,000

264009 MLS

Excellent investment and redevelopment opportunity! This TWO-BUILDING PORTFOLIO IS PRICED TOGETHER AS A PACKAGE and includes 2 Dufferin St. and 1 San Carlos Ave. Zoned CM-2, offering a variety of potential commercial, residential and mixed-use possibilities. 2 Dufferin Street was home to a successful hair salon for the past 20 years and is now vacant, ready for its next owner or business. 1 San Carlos Avenue is a duplex featuring a downstairs 2-bedroom, 1-bath unit (with the potential to be converted into a 3-bedroom, 1-bath) of approximately 1,398 SF, and an upstairs 2-bedroom, 1-bath unit of approximately 900 SF. Whether you're looking for income-producing rental properties, a live/work opportunity, or future redevelopment potential, this property offers flexibility and value. The two parcels provide approximately 10 parking spaces combined. Buyer to verify all measurements, zoning, permitted uses, and redevelopment potential.

1 E San Carlos Ave, St Augustine

$939,800

13 Beds ⋅ 8 Baths ⋅ G5117528 MLS

ATTENTION INVESTORS: (2) QUAD-PLEX BUILDINGS FOR SALE, (8) APARTMENT UNITS + (4) STORAGE UNITS PROVIDING $97,000.00+ IN ANNUAL CASH FLOW, EUSTIS, FL 32726. Located at 422 & 426 E. Citrus Avenue in the historic district of Eustis and just (3) Blocks from downtown. This is a "turnkey" investment opportunity, 100% occupancy, annual tenants, and provides a blended 6.925% CAP-RATE. These two separate quadplex buildings sit on .62 acres (115'x 232') with "NO HOA" and includes a combined heated 5,203 s/f and total size of 5,797 s/f. Both building are on City of Eustis water & sewer services. Building 422 Profile: (3-qty) 1-Bedroom, 1-Bath and (1-qty) 2-Bedroom, 1-BathUnits. All units were fully remodeled and updated in 2018. Building 426 Profile: (4-qty) 2-Bedroom, 1-Bath Units. All units were fully remodeled and updated in 2019. Building 426 also has a detached (4-qty) Rental Storage Units with Roll-Up Doors that also generate cash flow to the property. All units have (2) dedicated parking spaces each. Additionally, the property is located within close proximity & walking distance to Downtown Eustis & Bay Street, Lake Eustis lakefront, lots of restaurants, shops, city parks & just 5-minutes to the Lake County Mall, Target, Walmart, etc. and a variety of other conveniences for the tenants and their guests. Floor Plans & Seller Disclosures for each building & units are attached in the MLS, or available to be emailed. Detailed financials available to "Qualified Buyers" and includes full Unit Profiles, Upgrades/Improvements/Maintenance Info, Current & Past Income History, Expense Breakdown, Rental Comps Analysis for 1/1 & 2/1 rentals in the entire Eustis market. PLEASE DO NOT ENGAGE OR DISTURBANY OF THE TENANTS. NO SIGN at the property and all inquiries are to be directed "ONLY" to the Listing Broker. For reference, the purchase price includes the following properties: 422 E. Citrus Ave, Parcel ID#11-19-20-0100-076-00401, Alt Key#1759641 "and" 426 E. Citrus Ave, ParcelID#11-19-26-0100-076-00403, Alt. Key#1243122. Call directly for more information.

422 & 426 E Citrus Avenue, Eustis

$420,000

TB8545739 MLS

Excellent investment opportunity at 611 61st Ave Terrace E, Bradenton, FL! This duplex features two 1,200 sq. ft. units, each offering 3 bedrooms and 2 bathrooms. Each unit commands $2,195 per month, providing potential combined rental income of $4,390/month ($52,680 annually). The left unit is currently tenant occupied, while the right unit is vacant, giving a new owner the flexibility to place a tenant, occupy one side, or pursue other rental strategies. A similarly sized duplex with 2-bedroom/2-bath units recently sold for $425,000, providing a strong nearby point of comparison for this larger 3-bedroom configuration. Great opportunity for an investor seeking an income-producing multifamily property in Bradenton.

611 61st Avenue Terrace E, East Bradenton

$475,753

12 Beds ⋅ 8 Baths ⋅ OM731809 MLS

Easy to show! This well-maintained duplex features 2 bedrooms and 2 baths, DEN/3rd Bedroom and has been freshly painted inside and out. Enjoy peace of mind with a new roof (2024) and a new water heater (2024). All kitchen appliances are included. The spacious backyard offers plenty of room for outdoor activities and endless possibilities. Whether you are a first-time investor looking to expand your portfolio, or a buyer wanting to live in one unit while renting out the other, this income-producing property is full of potential!

4565 Sw 38th Place, Ocala

$450,000

4 Beds ⋅ 2 Baths ⋅ TB8546783 MLS

GREAT INVESTMENT OPPORTUNITY IN A PRIME LOCATION! Looking for an investment property where half the work is already done for you? This duplex is currently features two 2-bedroom, 1-bathroom units, with recently updated kitchens, bathrooms, and windows. Located in a desirable area with fishing access on Saint Joe’s Creek, this property offers a unique combination of investment potential and an appealing location. Each unit has its own living space, while a shared covered laundry room is conveniently located underneath the covered front porch. You have the flexibility to secure your own tenants, explore updated rental rates, or potentially occupy one unit while renting the other. Great location + two units + strong rental history = an opportunity you won’t want to miss! Schedule your showing today.

5000 74th Street N, Kenneth City

$475,753

12 Beds ⋅ 8 Baths ⋅ OM731811 MLS

This well-maintained duplex features 2 bedrooms and 2 baths, DEN/3rd Bedroom and has been freshly painted inside and out. Enjoy peace of mind with a new roof (2024) and a new water heater (2024). All kitchen appliances are included. The spacious backyard offers plenty of room for outdoor activities and endless possibilities. Whether you are a first-time investor looking to expand your portfolio, or a buyer wanting to live in one unit while renting out the other, this income-producing property is full of potential!

4540 Sw 38th Place, Ocala

$550,000

4 Beds ⋅ 4 Baths ⋅ TB8546775 MLS

Investors and owner-occupants, don’t miss this opportunity to own a duplex in Largo featuring two 2-bedroom, 2-bath units, each with its own electric and water meter. Both units are currently leased, and the existing tenants would love the opportunity to stay, offering the potential for immediate rental income and excellent investment potential. Whether you’re looking to expand your rental portfolio or live in one unit while renting the other, this property offers flexibility in a desirable Largo location. The roof is 7 years old. Sliding glass doors have been replaced. Yard is fenced in, allowing great space for pets or family gatherings. Opportunities like this don’t come along often! Call today to schedule your showing before it’s too late! Please note: The photos provided are only a selection of images from each unit and were taken prior to the current tenants moving in. The photos may not accurately represent the current colors or condition of the flooring, walls, bathrooms, or kitchens. Additional updates have been made since these photos were taken.

11316 Walsingham Road, Largo

$565,000

4 Beds ⋅ 5 Baths ⋅ TB8545347 MLS

Welcome home! Triplex just listed for Sale in Pinellas Park! Wonderful opportunity knocks for Investors looking to diversify their portfolio. 3-Unit Triplex is ready to go for the next owner. Recent 2026 refresh/renovations include: new flooring in each unit, some new appliances, sliding doors. New Roof in May 2026. Unit 1 is a Studio 1/1 with added porch space in the rear. Unit 2 is a 2/2 with Fireplace, and Laundry/Mud room. Unit 3 is the largest sq ft, 2/2 with huge enclosed Bonus room in the back. Each unit has a separate back yard space w/ Storage Shed. Plenty of shared parking out front with circle drive and option to make dedicated parking areas for each Unit. Make an appt soon as these investment opportunities do not come up often!

9845 60th Street, Pinellas Park