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$650,000
4 Beds ⋅ 2 Baths ⋅ A4703677 MLS
Fully renovated, income-producing duplex in a prime Sarasota location, perfect for investors or owner-occupants! This property has been completely redone with all work permitted, offering true peace of mind and zero deferred maintenance. Major upgrades include a new shingle roof, new AC systems, full electrical rewire, new plumbing, and impact-rated windows and doors for hurricane protection. Both units feature modern, move-in-ready interiors with tile flooring throughout, new drywall, updated cabinetry, and stainless steel appliances, making this a turnkey opportunity ready for immediate occupancy or rental. Situated on a quiet dead-end street, this property offers privacy while still being close to everything. Conveniently located just 3.8 miles to the beach and only 2.4 miles to Sarasota Memorial Hospital, with easy access to shopping, dining, and popular local restaurants, an ideal setup for strong and consistent rental demand. Whether you're looking to house hack, short- or long-term rent, or expand your portfolio, this fully upgraded duplex checks every box.

1802 Robinhood Street, South Sarasota

Listing courtesy of SAVVY AVENUE, LLC. 888-490-1268
$640,000
6 Beds ⋅ 6 Baths ⋅ TB8541085 MLS
Rare Find Sarasota duplex opportunity with a private swimming pool and exceptional flexibility for investors, multigenerational living, or an owner-occupant looking to generate rental income! Tucked away on a quiet cul-de-sac, 1213/1215 Benedict Ct offers two spacious units with a total of 6 bedrooms and 6 full bathrooms. Each unit features 3 bedrooms and 3 full baths, with every bedroom having access to its own full bathroom—an ideal layout for privacy, guests, extended family, or rental use. The property also offers mother-in-law suite functionality with a kitchenette for additional flexibility. One unit has been beautifully renovated, including an extensively renovated kitchen in approximately 2020, and is being offered fully furnished for a potential turnkey rental opportunity. Seller represents roof was replaced in approximately 2020; buyer to verify permitting, age, and condition. Enjoy the Florida lifestyle with a private swimming pool and patio area perfect for relaxing and entertaining. Additional highlights include two separate addresses and a versatile duplex configuration. Conveniently located near Downtown Sarasota with easy access to shopping, dining, entertainment, and Sarasota's world-famous Gulf Coast beaches. The property offers excellent potential for traditional, furnished, or short-term vacation rental use, subject to applicable City of Sarasota requirements. Live in one side and rent the other, accommodate extended family, or add a versatile Sarasota income property to your portfolio. Buyer and buyer's agent to verify room configuration, permitting, rental requirements, measurements, and all information deemed important to buyer.

1213 Benedict Court, Mid Town Sarasota

Listing courtesy of DALTON WADE INC. 888-668-8283
$499,900
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
$385,000
5 Beds ⋅ 3 Baths ⋅ A4702086 MLS
This property is gem in the rough, so close to downtown Sarasota and the Bay with a mixed-use zoning DTN, which falls under the Downtown Master Plan of 2020. Compared with conventional zoning that encourages development of Urban Communities that are diverse, compact and walkable. Plenty of possibilities in usage, height and added outbuildings. The current use is residential income producing with two units. Check this out, make future plans and be part of the Sarasota growth.

632/634 N East Avenue, Mid Town Sarasota

Listing courtesy of CENTURY 21 ROSEBAY. 941-366-7673
$425,000
6 Beds ⋅ 2 Baths ⋅ TB8537650 MLS
PRICED TO SELL. Beautifully Large Duplex with Income Potential – 121 & 123 Granada Blvd, North Port, FL 34287 6 beds | 2 baths | 2,304 sq ft | 7,534 sq ft lot | Zoned RMF-1 | No HOA| Not in Flood Zone This is a rare opportunity to own a spacious and income-generating duplex in one of North Port’s most desirable neighborhoods—Warm Mineral Springs. With 2,304 square feet of living space on a 7,534 square foot lot, this duplex combines long-term investment value with comfortable living. The property features two large 3-bedroom, 1-bath units (plus 1 unit has 1 shower and the other half bath), each with a private entrance, central air, and separate electric meters. One side offering a move-in-ready residence ideal for a homeowner, seasonal occupant, or short-term rental. Modern kitchen, bathroom and a separate shower, luxury vinyl plank flooring, interior paint in Benjamin Moore’s Chantilly Lace, and GFCI outlets throughout. The other unit is currently occupied by a long-term tenant, providing immediate and stable rental income. Tenant-occupied unit is in good condition; seller is happy to provide interior photos upon request. Tenants pay their own electricity, and with well and septic systems, overall utility costs are low. Roof replaced in 2017, offering peace of mind for years to come. Additional features include: • Private driveway parking for each unit • Ceiling fans throughout • Inside laundry • No HOA or deed restrictions—pets are welcome • One-story layout with slab foundation • Located outside flood zones. This property is ideally situated near schools, parks, shopping, beaches, and the famous Warm Mineral Springs, making it an excellent choice for homeowners and investors alike.

121 Granada Boulevard, North Port

Listing courtesy of LISTED SIMPLY. 800-995-5879
$1,300,000
4 Beds ⋅ 2 Baths ⋅ A4701927 MLS
Rare corner-lot duplex in Sarasota’s highly desirable Laurel Park Historic District, located approximately 0.5 miles from downtown Sarasota’s dining, shopping, arts, bayfront, and cultural attractions. Set beneath mature trees and surrounded by the timeless character of Laurel Park, this well-maintained property blends classic Old Florida charm with substantial recent improvements. Each residence offers 2 bedrooms, 1 bathroom, spacious living areas, a full kitchen, a dedicated laundry area, and its own private screened lanai overlooking fully fenced outdoor spaces that provide privacy and separation between the units. Recent improvements include a new roof installed in November 2024, new windows installed in September 2022, a full exterior repaint completed in January 2025, a remodeled bathroom, custom paver hardscaping, and refreshed landscaping. One residence also features a private putting green, a distinctive outdoor amenity rarely found near downtown Sarasota. Laurel Park is known for its historic character and convenient proximity to Burns Court, Payne Park, downtown Sarasota, and Sarasota Bay. Lido Key and Siesta Key beaches are also just a short drive away. Whether used as an owner-occupied residence with supplemental rental income, a long-term investment property, or a flexible downtown retreat, this duplex offers a variety of possibilities in one of Sarasota’s most charming and centrally located neighborhoods. An exceptional opportunity to own a versatile property offering character, privacy, recent improvements, and an outstanding downtown Sarasota location.

507 Madison Court, Downtown

Listing courtesy of EXP REALTY LLC. 888-883-8509
$251,900
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
$499,000
3 Beds ⋅ 2 Baths ⋅ A4701566 MLS
INVESTOR OPPORTUNITY! This fully furnished, income-producing duplex currently generates more than $60,000 annually, with the potential to further maximize its rental performance for an even higher return. Located just minutes from downtown Sarasota, the property offers two complete residences: a spacious two-bedroom, one-bath unit and a one-bedroom, one-bath unit. Each has its own kitchen, dining area, and living room. Both units are being sold turnkey, complete with furniture, kitchenware, bedding, linens, and a washer and dryer. Major improvements include a brand-new roof installed in 2025 and newer air-conditioning systems installed in 2022 and 2025. The current weekly housekeeping and turnover staff are also willing to remain in place, helping provide a smooth transition for the new owner. The City of Sarasota currently permits seven-day minimum rentals at this location, with the potential to apply for a certificate allowing shorter rental periods. Continue operating it as an established rental, occupy one unit while generating income from the other, or explore future redevelopment possibilities. New construction has become increasingly common along this street, creating an opportunity to generate income today while holding the property for its land value and long-term potential. Rental income and expenses are available for review. Rental regulations, zoning, and redevelopment options should be independently verified by the buyer.

2245 Bahia Vista Street, Central Sarasota

Listing courtesy of EXP REALTY LLC. 888-883-8509
$1,075,000
6 Beds ⋅ 4 Baths ⋅ A4701666 MLS
Discover this turnkey duplex — a fully updated 6-bed, 4-bath property (3 bedrooms and 2 baths per unit) offering exceptional income potential in a prime location. Each spacious unit features modern finishes and thoughtful layouts for comfortable living. Enjoy private oasis backyards with dedicated heated pools and fully fenced privacy on both sides — perfect for tenants seeking resort-style relaxation without sharing space. Separate entrances from Roselawn Street and Hansen Street. Recent upgrades include a new metal roof (2025) and comprehensive updates throughout, ensuring low maintenance and strong rental appeal. This duplex is an excellent investment, currently positioned to generate reliable income in a high-demand Sarasota rental market. Central Sarasota location provides easy access to world-famous Siesta Key Beach (minutes away via North Siesta Key Bridge), shopping, restaurants, parks, and everyday conveniences. Quick drives to downtown Sarasota, I-75 make it ideal for residents and investors alike. Whether you're expanding your portfolio or seeking a smart income-producing property, this updated duplex delivers value, privacy, and location in one package. Don't miss out — schedule a showing today!From Bee Ridge Rd, Turn South on School, North on Hansen or Roselawn St. Go to address. From US41 Turn East on Roselawn and go to address.

2047 Roselawn Street, South Sarasota

Listing courtesy of WILLIAM RAVEIS - FLORIDA LLC. 941-867-3901
$1,000,000
8 Beds ⋅ 8 Baths ⋅ A4701436 MLS
Virtually Staged. Cash flow in paradise! This is a great Sarasota investment opportunity featuring two side-by-side duplexes with four rentable units sold together as one package, tucked on a quiet street just minutes from the sugar sand of Siesta Key and across the way from the newly updated Landings Plaza with its new shops and restaurants. Whether you are growing a portfolio or making your first multifamily move, the expensive work is already done here, leaving a true turnkey asset of solid one-story block construction with tastefully renovated units and updated major systems throughout. Both buildings received brand new roofs in 2024, fully permitted, complete with sealed roof decks and third-nail wind mitigation retrofits, and current wind mitigation reports are in hand that may help qualify for insurance premium reductions. Upgrades since 2023 also include new electrical panels in all four units, full attic ductwork replacement, a new A/C in one unit, cast-iron drain line remediation, and kitchen and bath remodels in select units. Each unit offers 2 bedrooms, a full bath, and a convenient half bath located in the primary bedroom, along with a private entrance, in-unit washer and dryer, wood-look luxury vinyl plank flooring, ceiling fans, generous storage, and its own yard space with off-street parking beneath mature mango and shade trees. With the Landings Plaza at the doorstep, the Gulf Gate corridor, the Legacy Trail, and the beaches all minutes away, year-round rental demand takes care of itself. The duplexes sit on two separate tax parcels but are offered together as a package only and will not be sold individually. Capital improvements summary, wind mitigation reports, and closed roof permits available. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

2047 & 2051 Fiesta Drive, South Sarasota

Listing courtesy of KW COASTAL LIVING III. murraycoleman@kw.com
$499,000
5 Beds ⋅ 4 Baths ⋅ A4701355 MLS
Rare opportunity to own two separate homes on one legally established parcel in the heart of Sarasota. Set on an oversized 0.38-acre double lot in desirable DeSoto Lakes, this property offers incredible flexibility for homeowners, investors, and multi-generational living. While the interiors are ready for your personal vision and cosmetic touches, the costly updates are already done making it FULLY FINANCEABLE AND INSUREABLE. Brand new roof, July 2026. Brand new central A/C in the main home, July2026. New split system A/Cs in the smaller home, July 2026. New water heater and brand new windows throughout, July 2026. Brand new electric panel, July 2026. The main home features four bedrooms, three baths, and just under 1800 square feet. The detached second home is a true one-bed, one-bath residence with five hundred and seventy-two square feet. Live in one, rent the other to help offset your mortgage. Lease both for investment income. Carve out a suite within the main home for added flexibility or enjoy a private guest house for friends and family. Buyers may also explore future redevelopment options. Location, location, location. You are minutes to University Town Center, US-41, I-75, SRQ Airport, Downtown Sarasota, Downtown Bradenton, and our world-famous Gulf Beaches. This is a rare chance to secure a versatile property in one of Sarasota's most connected pockets, priced to sell and ready for your vision.

4734 Delmonte Avenue, The Meadows

Listing courtesy of PREFERRED SHORE LLC. 941-999-1179
$524,995
4 Beds ⋅ 2 Baths ⋅ A4701097 MLS
Investor Opportunity or Ideal Owner-Occupant Duplex in Desirable Southgate – Sarasota, FL Exceptional opportunity to own a solid block construction duplex in the highly sought-after Southgate area of Sarasota. Offered at $524,995, this versatile, well-maintained property is perfect for investors seeking reliable rental income or buyers looking to live in one unit while generating income from the other. With no HOA and separate electric and water meters for each unit, this property offers the flexibility and convenience today’s buyers and investors are looking for. Each spacious unit features 2 bedrooms, 1 full bathroom, an open-concept kitchen, dining area, and a comfortable great room, creating a bright, inviting living space that appeals to both homeowners and tenants. Ceramic tile flooring throughout provides durability, easy maintenance, and a clean, timeless look. Each unit also includes a pantry/laundry room with washer and dryer hookups, adding valuable storage and everyday convenience. A convenient two-car carport is located between the units, providing covered parking and additional convenience for both residences. This property has been meticulously maintained and offers numerous valuable updates that provide peace of mind for years to come. Highlights include a 75-year-rated metal roof installed approximately eight years ago, HVAC systems replaced within the last four and five years, respectively, and newer water heaters in both units. The beautifully landscaped grounds reflect pride of ownership and enhance the property’s curb appeal. Location is one of this property’s greatest assets. Nestled in the established Southgate neighborhood, you’ll enjoy the convenience of being just 10 minutes from vibrant downtown Sarasota, where exceptional dining, shopping, arts, entertainment, and cultural attractions await. Even better, you’re only 15 minutes from the world-renowned white sands of Siesta Key Beach and beautiful Lido Beach, making this an outstanding location for both residents and tenants alike. Whether you’re expanding your investment portfolio, searching for a multi-generational living opportunity, or looking to offset your mortgage with rental income, this duplex offers exceptional value in one of Sarasota’s most desirable and centrally located neighborhoods. Don’t miss this rare opportunity to own a move-in-ready, income-producing property in the heart of Sarasota.

2911 Bentley Street, Central Sarasota

Listing courtesy of SAVVY AVENUE, LLC. 888-490-1268
$449,900
4 Beds ⋅ 2 Baths ⋅ A4700880 MLS
Attention income seekers: here's a full duplex where two complete homes share one smart investment, each offering two bedrooms, one bath, and a floor plan ready to put money to work. With 1,694 square feet spread across both sides, this property practically hands you a built-in revenue stream from the moment you turn the key. The math is refreshingly straightforward. Two rentable units mean two monthly checks, giving you the flexibility to lease both for maximum yield or live in one while the other quietly covers your costs. Each home comes equipped with a range, refrigerator, and its own washer and dryer—amenities that keep tenants happy and turnover low. Better still, the property carries genuine renovation upside; a few thoughtful updates could lift rents and boost your return in short order. Location does plenty of the heavy lifting when it comes to attracting quality renters. Sprouts Farmers Market sits practically next door for effortless grocery runs, while Wharf Road Park offers green space for weekend leisure just around the corner. A nearby bus stop along Tamiami Trail keeps tenants well connected, and the surrounding Sarasota neighborhood adds steady demand that landlords love. Whether you're building a rental portfolio, seeking a house-hack that pays your mortgage, or simply chasing dependable cash flow, this duplex delivers the fundamentals plus room to grow. Opportunities that combine location, layout, and upside like this move quickly. Schedule your private showing today and start counting the returns. New Septic System being installed.

1805 Marbeth Street Unit 1805/1807, South Sarasota

Listing courtesy of EXP REALTY LLC. 888-883-8509
$344,900
5 Beds ⋅ 3 Baths ⋅ D6147971 MLS
Searching for the perfect investment opportunity? This duplex could be exactly what you've been looking for! Both units are currently tenant-occupied, providing immediate rental income from day one. Even better, both units have been remodeled within the past few years, and a brand-new roof was installed in 2023 for added peace of mind. One unit features 3 bedrooms and 2 bathrooms, while the other offers 2 bedrooms and 1 bathroom, making this property appealing to a variety of tenants. Location is another standout feature! Nestled in a peaceful residential neighborhood in North Port, Florida, this property offers convenient access to schools, parks, shopping, dining, recreation centers, beautiful Gulf Coast beaches, and the world-famous Warm Mineral Springs. It's a highly desirable area that continues to attract renters. Whether you're expanding your real estate portfolio or purchasing your first investment property, this duplex offers an excellent opportunity for dependable rental income and long-term growth. With immediate cash flow, recent updates, and a prime location, this is an investment you won't want to miss!

12100 Capilla Lane, North Port

Listing courtesy of GULF REALTY LLC. 775-287-7680
$650,000
8 Beds ⋅ 8 Baths ⋅ A4699168 MLS
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, Central Sarasota

Listing courtesy of RE/MAX ALLIANCE GROUP. 941-954-5454
$469,777
4 Beds ⋅ 2 Baths ⋅ A4697614 MLS
Excellent opportunity to own a well-maintained duplex in a highly desirable Sarasota location just minutes from world-famous Siesta Key Beach, Downtown Sarasota, shopping, dining, and transit. This property features two separate 2-bedroom, 1-bathroom units, making it ideal for investors seeking strong rental income or owner-occupants looking to offset their mortgage with rental revenue. Both entrances have enclosed lanai areas. The front unit lanai has laundry hookups. Tile flooring throughout, large kitchens, tub with tiled shower walls. Ceiling fans in bedrooms. Fenced on back and side of building. Both units offer comfortable floor plans with central air conditioning and charming fireplaces that add character and appeal. The rear unit includes a valuable two-car carport, dedicated storage area, and laundry hookups, providing additional convenience for tenants. 2011 Metal Roof, 2021 & 2022 HVAC. Owner pays water, electric separately metered. Attractive units and setup for long-term renters. Situated on a quiet street with easy access to Sarasota's beaches, cultural attractions, restaurants, and everyday conveniences, this duplex combines location, functionality, and investment potential. Buyer to verify all measurements, rental information, and property details.

2110 Palm Terrace, South Sarasota

Listing courtesy of RELAX PROPERTY GROUP, LLC. 941-923-7200
$449,777
5 Beds ⋅ 2 Baths ⋅ A4697057 MLS
Rare investment opportunity in Sarasota! Multi-family properties are seldom available in this predominantly single-family neighborhood, making this duplex a unique addition to any real estate portfolio. This income-producing property offers two separately leased units with a combined living area of approximately 1,818 square feet on a 7,800-square-foot lot. The front unit features 3 bedrooms, 1 bathroom, & a dedicated laundry room while the second (Back) unit offers 2 bedrooms, 1 bathroom, and backyard access. Both units are currently occupied through 3/31/2026, providing immediate rental income and minimizing vacancy risk for investors seeking stable cash flow. Electric/Water are not separately metered and Landlord pays these two utilities. Several major improvements have already been completed, including a new roof in 2019, updated HVAC in 2023 (back unit uses window units), and an updated electrical panel in 2023. The property is in the central Sarasota area with easy access to shopping, dining, schools, employment centers, downtown Sarasota, and the area's world-famous Gulf Coast beaches. Gross rents of $4,010. Annual Leases. Seller will consider owner financing. Showings require advanced notice. Call today!

3731 Papai Drive, Central Sarasota

Listing courtesy of RELAX PROPERTY GROUP, LLC. 941-923-7200
$2,895,000
5 Beds ⋅ 7 Baths ⋅ A4694972 MLS
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.

Siesta Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-349-3444
$2,895,000
5 Beds ⋅ 7 Baths ⋅ A4694978 MLS ⋅ 6910 B BLDG.
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, Siesta Key

Listing courtesy of MICHAEL SAUNDERS & COMPANY. 941-349-3444
$990,000
6 Beds ⋅ 6 Baths ⋅ A4696057 MLS
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, South Sarasota

Listing courtesy of THE MULTIFAMILY FIRM LLC. 941-444-6160
$450,000
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
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
$575,000
1 Beds ⋅ 1 Baths ⋅ P4938368 MLS
PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!

6006 Midnight Pass Road Unit 51, Siesta Key

Listing courtesy of HUT REALTY, LLC. 407-559-2929
$649,000
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
$380,000
4 Beds ⋅ 2 Baths ⋅ A4687286 MLS ⋅ 6231 And 6221 BLDG.
Rare and exceptional turnkey investment opportunity just 3 miles from Warm Mineral Springs Park in beautiful North Port! This well maintained duplex features a total of 4 bedrooms and 2 bathrooms, with each unit offering 2 spacious bedrooms and 1 full bath perfect for long-term tenants or short-term rental opportunities like Airbnb. Recent upgrades add tremendous value and peace of mind, including newly updated kitchen cabinets with elegant granite countertops, durable tile flooring throughout, brand new electrical panels with updated electrical systems, and newly painted exterior. With no HOA restrictions, enjoy maximum flexibility, live in one unit while renting the other, or lease both sides for strong, consistent cash flow. Ideally situated in a desirable, central neighborhood, the property is just minutes from shopping, dining, schools, and everyday essentials. Plus, you’re only 15 miles from Manasota Beach, offering easy access to Florida’s beautiful Gulf Coast lifestyle. Whether you’re an investor seeking reliable income or a homeowner looking to offset your mortgage, this high-demand duplex checks all the boxes.

6231 Coniston Terrace, North Port

Listing courtesy of DALTON WADE INC. 888-668-8283
$380,000
4 Beds ⋅ 2 Baths ⋅ N6143422 MLS
LOCATION! POTENTIAL! Excellent opportunity to own a beautiful short-term or long-term rental property just walking distance to the world-famous Warm Mineral Springs! This property offers strong investment potential in one of the most desirable areas of North Port.NOT FLOOD ZONE! NICELY UPDATED! Both units feature tile flooring throughout, a beautiful modern kitchen with granite countertops, tile backsplash, stainless steel appliances, and fully equipped kitchens. The bathrooms have been completely remodeled, and each unit includes its own laundry area for added convenience. Major updates completed : include electric panels, water filtration system, windows, gutters, and paved driveway, giving buyers peace of mind. Each unit also offers a full carport plus additional paved driveway parking. Additional features include a storage shed in the backyard and solid mechanical updates: Roof (2025), both drainfields replaced in November 2012, NEW WELL & PUMP 2025,A/C in Unit 1 (2015) and Unit 2 (August 2018). Located close to shopping, restaurants, banking, and medical facilities, and only 15–20 minutes from the beautiful Gulf beaches in Venice and Englewood. Nothing to do but start generating income. Don’t delay—schedule your showing today!

12125 Margarita Avenue, North Port

Listing courtesy of RE/MAX PALM REALTY OF VENICE. 941-451-2025
$699,000
4 Beds ⋅ 4 Baths ⋅ A4686063 MLS ⋅ 2214 BLDG.
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, South Sarasota

Listing courtesy of KELLER WILLIAMS ON THE WATER S. 941-803-7522
$1,050,000
6 Beds ⋅ 5 Baths ⋅ A4682694 MLS
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, South Sarasota

Listing courtesy of WILLIAM RAVEIS REAL ESTATE. 941-867-3901
$480,000
4 Beds ⋅ 2 Baths ⋅ A4677334 MLS
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, Mid Town Sarasota

Listing courtesy of REALTY SOLUTIONS SRQ. 941-492-0784
$1,129,000
4 Beds ⋅ 4 Baths ⋅ C7520010 MLS
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, Osprey/Nokomis

Listing courtesy of PREMIER PROPERTIES OF SRQ LLC. 941-526-3113

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