Rare investment opportunity in Sarasota's highly sought-after Indian Beach neighborhood for under $800K! This vintage mid-century 4-plex features durable concrete block construction, thoughtfully designed as two facing duplexes surrounding a private, complex-only pool. Each of the 4 units offers 2 bedrooms, 1 bathroom, its own dedicated carport, and an individual laundry room for maximum tenant convenience. The back two units highlight recent remodeling upgrades and new appliances. With 2 units currently rented below market value, & 2 still vacant, this property offers immediate upside potential and increased cash flow for investors. Unbeatable location just minutes from Ringling College, Downtown Sarasota, US-41, and local beaches. Don't miss this high-demand, low-turnover income generator!

8 Beds ⋅ 4 Baths ⋅ A4701502 MLS

Rare investment opportunity in Sarasota's highly sought-after Indian Beach neighborhood for under $800K! This vintage mid-century 4-plex features durable concrete block construction, thoughtfully designed as two facing duplexes surrounding a private, complex-only pool. Each of the 4 units offers 2 bedrooms, 1 bathroom, its own dedicated carport, and an individual laundry room for maximum tenant convenience. The back two units highlight recent remodeling upgrades and new appliances. With 2 units currently rented below market value, & 2 still vacant, this property offers immediate upside potential and increased cash flow for investors. Unbeatable location just minutes from Ringling College, Downtown Sarasota, US-41, and local beaches. Don't miss this high-demand, low-turnover income generator!

3509 Norwood Court, North Sarasota

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-966-8000

$499,900

Virtually Staged. Updated duplex with private pool and new roof in Prime location only 1/2 mile to Sarasota Bay and Bay Shore Rd with million dollar homes. The property features two separate 2 BD 2BA units which are both included. The front Unit A is currently rented for $1,600/mo & the rear unit B is vacant with a rental estimate between $1750-$1800/mp. Live in one side and rent the other or rent them both! Both units have same sq ft L/A of 899 sq ft but are slightly different. Unit A has a fireplace in the living rm. New roof in 2025. Additional updates include appliances, cabinets, flooring & water heater. Lots of parking with the tandem style driveway. Prime location just minutes to downtown Sarasota, Ringling School of Art, Jungle Gardens, Univeristy of South Florida, Bayfront and so much more! Great investment opportunity in prime Sarasota location!

4 Beds ⋅ 4 Baths ⋅ A4702687 MLS

Virtually Staged. Updated duplex with private pool and new roof in Prime location only 1/2 mile to Sarasota Bay and Bay Shore Rd with million dollar homes. The property features two separate 2 BD 2BA units which are both included. The front Unit A is currently rented for $1,600/mo & the rear unit B is vacant with a rental estimate between $1750-$1800/mp. Live in one side and rent the other or rent them both! Both units have same sq ft L/A of 899 sq ft but are slightly different. Unit A has a fireplace in the living rm. New roof in 2025. Additional updates include appliances, cabinets, flooring & water heater. Lots of parking with the tandem style driveway. Prime location just minutes to downtown Sarasota, Ringling School of Art, Jungle Gardens, Univeristy of South Florida, Bayfront and so much more! Great investment opportunity in prime Sarasota location!

1003 Patterson Drive, North Sarasota

Listing courtesy of VIRTUAL REALTY OF FLORIDA. 954-999-2958

$251,900

<BACK ON THE MARKET><LAST PRICE REDUCTION> INVESTOR SPECIAL in one of Sarasota's most desirable and rapidly growing neighborhoods! This unique abandoned duplex is packed with potential and ready for its next chapter. Situated on an oversized lot and currently vacant, this versatile property presents an outstanding opportunity for investors seeking a fix-and-flip, a long-term cash-flowing rental, or an owner-occupant looking to live in one unit while generating income from the other. With strong upside and endless possibilities, this is a rare chance to add value in an area experiencing continued growth. From the moment you arrive, the property offers excellent functionality and accessibility with a spacious covered carport providing protected parking and additional covered outdoor living space. A fully fenced front yard with gated entry enhances privacy while allowing convenient street access. Each unit features its own private entrance, making the layout ideal for tenants, multigenerational living, or house hacking. A covered walkway connects both units, while the expansive front and side yards provide ample space for additional parking, outdoor entertaining, or future improvements. The simple, low-maintenance exterior creates a solid foundation for renovation while maximizing long-term investment potential. Inside, one of the units features a functional layout with an open living and dining area that flows into the kitchen, creating an efficient use of space. Durable ceramic tile flooring extends throughout the home, while the kitchen offers generous cabinet and countertop space with excellent potential for modernization. The bedrooms are comfortably sized with built-in closets, and the full bathroom includes a tub/shower combination and practical layout. An attached utility and storage room provides additional flexibility for laundry, storage, or workshop space. This unit would benefit from cosmetic updates, making it an excellent value-add opportunity to increase equity and rental income. The second unit is currently secured, and keys are not presently available; however, the entire property is vacant, and the second unit is believed to offer a substantially similar floor plan and layout. Buyers are encouraged to verify all room dimensions, features, and condition during their own due diligence. Major improvements include a brand-new roof installed in 2023, providing significant value and peace of mind. Utilities are currently off. With no HOA and no rental restrictions, this property offers exceptional flexibility for both short- and long-term investment strategies. Whether you're looking to renovate and resell, build a long-term income-producing asset, or occupy one unit while renting the other, this Sarasota duplex offers incredible potential. Property is being sold as-is.

4 Beds ⋅ 2 Baths ⋅ TB8536167 MLS

<BACK ON THE MARKET><LAST PRICE REDUCTION> INVESTOR SPECIAL in one of Sarasota's most desirable and rapidly growing neighborhoods! This unique abandoned duplex is packed with potential and ready for its next chapter. Situated on an oversized lot and currently vacant, this versatile property presents an outstanding opportunity for investors seeking a fix-and-flip, a long-term cash-flowing rental, or an owner-occupant looking to live in one unit while generating income from the other. With strong upside and endless possibilities, this is a rare chance to add value in an area experiencing continued growth. From the moment you arrive, the property offers excellent functionality and accessibility with a spacious covered carport providing protected parking and additional covered outdoor living space. A fully fenced front yard with gated entry enhances privacy while allowing convenient street access. Each unit features its own private entrance, making the layout ideal for tenants, multigenerational living, or house hacking. A covered walkway connects both units, while the expansive front and side yards provide ample space for additional parking, outdoor entertaining, or future improvements. The simple, low-maintenance exterior creates a solid foundation for renovation while maximizing long-term investment potential. Inside, one of the units features a functional layout with an open living and dining area that flows into the kitchen, creating an efficient use of space. Durable ceramic tile flooring extends throughout the home, while the kitchen offers generous cabinet and countertop space with excellent potential for modernization. The bedrooms are comfortably sized with built-in closets, and the full bathroom includes a tub/shower combination and practical layout. An attached utility and storage room provides additional flexibility for laundry, storage, or workshop space. This unit would benefit from cosmetic updates, making it an excellent value-add opportunity to increase equity and rental income. The second unit is currently secured, and keys are not presently available; however, the entire property is vacant, and the second unit is believed to offer a substantially similar floor plan and layout. Buyers are encouraged to verify all room dimensions, features, and condition during their own due diligence. Major improvements include a brand-new roof installed in 2023, providing significant value and peace of mind. Utilities are currently off. With no HOA and no rental restrictions, this property offers exceptional flexibility for both short- and long-term investment strategies. Whether you're looking to renovate and resell, build a long-term income-producing asset, or occupy one unit while renting the other, this Sarasota duplex offers incredible potential. Property is being sold as-is.

1764 24th Street, North Sarasota

Listing courtesy of RICHARD PETERS REALTY LLC. 352-448-9712

$524,900

Under contract-accepting backup offers. 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

3 Beds ⋅ 4 Baths ⋅ A4700635 MLS

Under contract-accepting backup offers. 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, North Sarasota

Listing courtesy of HARRY ROBBINS ASSOC INC. 941-924-8346

$450,000

Unit A is currently owner-occupied, while Unit B—previously operated as a short-term rental—has recently been converted to a long-term rental with a tenant paying $2,050 monthly, excluding utilities. This current setup perfectly demonstrates the property’s income flexibility and “house hacking” potential, allowing an owner-occupant to live in one unit while generating rental income from the other. 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. The current owners originally purchased the property using FHA financing as their primary residence, further illustrating the property’s potential 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.

4 Beds ⋅ 2 Baths ⋅ A4694443 MLS

Unit A is currently owner-occupied, while Unit B—previously operated as a short-term rental—has recently been converted to a long-term rental with a tenant paying $2,050 monthly, excluding utilities. This current setup perfectly demonstrates the property’s income flexibility and “house hacking” potential, allowing an owner-occupant to live in one unit while generating rental income from the other. 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. The current owners originally purchased the property using FHA financing as their primary residence, further illustrating the property’s potential 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, North Sarasota

Listing courtesy of DALTON WADE INC. 888-668-8283

$429,000

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.

5 Beds ⋅ 2 Baths ⋅ O6397687 MLS

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, North Sarasota

Listing courtesy of BLUE PEAK REALTY LLC. 727-777-7100

$649,000

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.

3 Beds ⋅ 2 Baths ⋅ A4688859 MLS

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, North Sarasota

Listing courtesy of COLDWELL BANKER REALTY. 941-366-8070

$669,000

Under contract-accepting backup offers. 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.

4 Beds ⋅ 4 Baths ⋅ A4679926 MLS

Under contract-accepting backup offers. 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, North Sarasota

Listing courtesy of KELLER WILLIAMS ON THE WATER S. 941-803-7522