Oakland Sub Real Estate, Homes, Condos for Sale in Dunedin, FL

Prime opportunity to own a free-standing mixed-use luxury building positioned on a busy, signalized corner at Main St. and Bass Blvd. in the heart of the Dunedin Downtown Core zoning district. This modern two-story block construction (built 2009) offers exceptional visibility, strong daily activity, and a flexible layout suited for a wide range of commercial or live-work uses. Located directly across from the new bank and a popular restaurant, the property benefits from consistent foot traffic and a 17,000 vehicles-per-day traffic count. The building features 3,333 sq ft of conditioned space, an elevator, a two-car garage, and 10 dedicated parking spaces — a rare advantage in the downtown corridor. Ideal for an owner-operator who wants to work downstairs and live upstairs, or for a business seeking to commercially utilize the entire building. The structure’s luxury finishes, strong corner presence, and adaptable floor plan make it an outstanding choice for retail, office, professional services, or boutique commercial concepts. A standout asset in one of Dunedin’s most desirable and walkable districts — offering visibility, versatility, and long-term value.

1000 Bass Boulevard, Dunedin

$1,325,000

Oakland Sub SubDv. ⋅ 34698 Zip Code

A rare opportunity to own a well maintained six unit, one floor apartment complex in desirable Dunedin. Five 2 bedroom, and one 1 bedroom units. With attached laundry room. Block building. 10 parking spaces. Built in 1986. Currently rented below market value on a month to month basis. New roof in 2020. All units have their own split system central A/C. No flood insurance required. Close to everything that Desirable Dunedin has to offer, and across from Mease Manor.

744 Mease Plaza, Dunedin

$1,150,000

Oakland Sub SubDv. ⋅ 34698 Zip Code

Prime Downtown Dunedin Investment Opportunity 4 UNITS! – No Rental Restrictions and zoned Downtown Core and commercial as well! $167,899 in net income total for the last 2 years(total of 2023 & 2024)! Amazing & a rare opportunity to own a turnkey, income-producing property in the heart of Downtown Dunedin! This fully renovated and beautifully furnished multi-unit property offers four short-term rental units currently listed on Airbnb and other vacation rental platforms, making it an exceptional investment with endless possibilities. The front building features two separate units each 2 bed 2 bath with primary suites in each, which can be rented individually or combined to create a spacious 4-bedroom, 4-bath home for larger groups. The rear building offers two additional 1-bedroom, 1-bath units, one on each floor, providing flexibility for rental income or personal use. Convenient alleyway access allows for ample rear parking, with additional parking available along the sides. A shared community lounge area and grill station create a welcoming outdoor space for guests to relax and enjoy the Florida lifestyle. Zoned Downtown CORE with NO rental restrictions, this property is more than just an investment—it’s an opportunity! Whether you continue operating it as a thriving short-term rental business, live in one building and rent out the other, or explore options like a coffee shop, bar, office, or boutique storefront, the potential is limitless. Don’t miss this rare chance to own a highly desirable property just steps from Downtown Dunedin’s top restaurants, shops, breweries, and the Pinellas Trail. Schedule your private tour today! Seller is open to seller financing with right terms. Call today for more information!

742 Main Street, Dunedin

$1,150,000

6 Beds ⋅ 4 Baths ⋅ Oakland Sub SubDv. ⋅ 34698 Zip Code

Prime Downtown Dunedin Investment Opportunity 4 UNITS! – No Rental Restrictions and zoned Downtown Core and commercial as well! $167,899 in net income total for the last 2 years(total of 2023 & 2024)! Amazing & a rare opportunity to own a turnkey, income-producing property in the heart of Downtown Dunedin! This fully renovated and beautifully furnished multi-unit property offers four short-term rental units currently listed on Airbnb and other vacation rental platforms, making it an exceptional investment with endless possibilities. The front building features two separate units each 2 bed 2 bath with primary suites in each, which can be rented individually or combined to create a spacious 4-bedroom, 4-bath home for larger groups. The rear building offers two additional 1-bedroom, 1-bath units, one on each floor, providing flexibility for rental income or personal use. Convenient alleyway access allows for ample rear parking, with additional parking available along the sides. A shared community lounge area and grill station create a welcoming outdoor space for guests to relax and enjoy the Florida lifestyle. Zoned Downtown CORE with NO rental restrictions, this property is more than just an investment—it’s an opportunity! Whether you continue operating it as a thriving short-term rental business, live in one building and rent out the other, or explore options like a coffee shop, bar, office, or boutique storefront, the potential is limitless. Don’t miss this rare chance to own a highly desirable property just steps from Downtown Dunedin’s top restaurants, shops, breweries, and the Pinellas Trail. Schedule your private tour today! Seller is open to seller financing with right terms. Call today for more information!

742 Main Street, Dunedin

$1,375,000

5 Beds ⋅ 4 Baths ⋅ Oakland Sub SubDv. ⋅ 34698 Zip Code

BRAND NEW CUSTOM BUILT ALL BLOCK CONSTRUCTION 5 BEDROOM HOME AT THE FOUR CORNERS OF AMERICA’s HOMETOWN, DUNEDIN, FLORIDA. FROM A BREATHTAKING FRONT FACADE FRAMED IN CONTRASTING BLACK AND WHITE TRIM, CHICAGO BRICK & BESPOKE DESIGNER GARAGE & ENTRY DOORS TO A LEVEL 5 SKIM FINISH THROUGHOUT THE MAGNIFICENT INTERIORS, THIS EXQUISITE RESIDENCE WILL ENTHRALL YOUR SIGHT & SENSES. From the word go just beyond that aforementioned front entry door belies a floor plan conducive to an integrated modern feel that allows for superb and gracious year round family living. An impressive large scaled great room, dining and kitchen arena take center stage for every entertaining, gathering and social experience while a first floor full bedroom and full bath rest adjacent. An ascending staircase ushers in 4 more bedrooms inclusive of the Primary Suite, it’s spectacular spa bath, windowed volume walk-in closet, a Garden suite w/accompanying en-suite, and two more bedrooms w/ a modern day Jack n Jill en-suite bath. A well cushioned upstairs landing affords a sitting area, children’s and/or adults rec space. Presented in a nuanced paint treatment, timeless lighting, superior plank flooring, custom through and through Italian KIOS kitchen, bath, closet and storage CABINETRY, stone counters, world worthy status appliances, ethereally chic tile, textile and stone encased baths the interiors lend to a life well lived. Architecturally balanced volume ceilings, miles of recessed lighting, masterful mill work, a butlers pantry, a laundry center, 2+car garage and a VOLUMINOUS BACK YARD AWAIT WITHIN THIS GEOGRAPHICALLY BLESSED MODERN MAYBERRY.

1046 Bass Boulevard, Dunedin

$685,000

3 Beds ⋅ 2 Baths ⋅ Oakland Sub SubDv. ⋅ 34698 Zip Code

THE SELLER WILLING TO PAY THE DOWN PAYMENT FOR BUYERS!!! Seize this rare opportunity to own a versatile property in the heart of Downtown Dunedin, ideal for short- or long-term rentals! Currently operating as a highly successful Airbnb, this fully updated 3-bedroom, 2-bath home is zoned for both commercial and residential use, offering endless potential. Situated in one of Florida’s most sought-after tourist destinations, this 1930s bungalow Cottage effortlessly combines historic charm with modern upgrades. Guests will love its prime location, allowing them to walk to breweries, golf cart to local restaurants, bike the scenic Pinellas Trail, or enjoy sunsets at the nearby waterfront—all just steps from the front door. This home boasts numerous updates, including a new AC system, upgraded power panel, and a brand-new kitchen with shaker cabinets, stainless steel appliances, soft-close drawers, quartz countertops, and an under-mount sink. The original hardwood floors blend seamlessly with new wood-look vinyl flooring, while both bathrooms have been completely remodeled. Natural light fills the space, and the fenced-in backyard, complete with pavers and a hot tub, creates the perfect spot for entertaining. The property also features fresh landscaping and exterior paint. With no rental restrictions, Downtown Core (DC) zoning, no flood zone designation, and fully furnished, this investment is ready to generate income from daily, weekly, monthly, or yearly rentals. Don’t miss this incredible chance to turn dreams into reality—whether for yourself or your guests! Property is being sold completely furnished, turnkey VRBO & AirBnB.

1000 Oak Street, Dunedin

$1,235,000

5 Beds ⋅ 4 Baths ⋅ Oakland Sub SubDv. ⋅ 34698 Zip Code

One or more photo(s) has been virtually staged. CUSTOM BUILT BRAND NEW FIVE BEDROOM & 4 BATH 3,000 SQ.FT. CONSTRUCTION HOME WITHIN THE EPICENTER OF AMERICA’S HOMETOWN, DUNEDIN. LITERALLY FINISHED TWO AND ONE HALF WEEKS AGO. 3/4 OF ONE BLOCK TO EVERY QUAINT SHOPPE, MICRO& GASTRO PUB, FINE & CASUAL EATERY, AND 4 BLOCKS TO DUNEDIN’S MARINA, WATERFRONT PARK, AND IT’S LEGENDARY SHORELINE. APPROXIMATELY A 4 MINUTE DRIVE TO COUNTRYSIDE WITH ITS’ VAST ARRAY OF DINING, ENTERTAINING, AND SHOPPING VENUES. APPOINTED W/ A LEVEL 5 SKIM COATED WALL & CEILING FINISH, VOLUME CEILINGS, SOLID CORE DOORS, TIMELESS MILL WORK, BESPOKE ITALIAN KIOS CABINETRY, QUARTZ ISLAND, STONE COUNTERS, EXQUISITE CULINARY APPLIANCES, REFINED PLANK FLOORING, MODERN, YET ORGANIC BATHS. THE PRIMARY SUITE ENJOYS TWO WALK-IN CLOSETS, AND ITS OWN SPA BATH. A GARDEN SIDE SUITE SERVES AS ITS’ OWN SANCTUARY, WHILE 2 MORE BEDROOMS SHARE A JACK N’JILL BATH. AN UPSTAIRS LANDING WILL SERVE ITS’ FUTURE OWNERS WELL AS AN ADDITIONAL DEDICATED FAMILY SPACE. THE DOWNSTAIRS INTEGRATION ALLOWS A SEAMLESS FAMILY ROOM, DINING & KITCHEN EMPORIUM. A 5TH BEDROOM W/ FULL HALL BATH IS CONVENIENTLY LOCATED ON THIS LEVEL, BUT MAY ALSO BE UTILIZED AS A HOME OFFICE, OR GUEST BEDROOM. A 2 CAR GARAGE, VOLUME BACKYARD, AND A NEW WORLD CRAFTSMAN FACADE AWAIT... The buyer is advised to independently verify the accuracy of all the measurements.

1044 Bass Boulevard, Dunedin

$590,000

2 Beds ⋅ 1 Baths ⋅ Oakland Sub SubDv. ⋅ 34698 Zip Code

MOVE IN READY or use as a COMMERCIAL /INCOME PRODUCING RENTAL. This unique 1920’s Bungalow in the DOWNTOWN CORE District of Dunedin is zoned MIXED USE and can be used for Commercial, Retail, Office, or Residential space!! This beautiful home has been completely renovated with no expense spared. This property features new modern amenities while still preserving all the charm of a historical bungalow. High ceilings, refinished and restored hard wood floors, and gorgeous tile in the bathroom and kitchen. Beautiful Shiplap throughout while exquisite chandlers and recessed lighting illuminate the space. All newer windows, along with updated Plumbing, Electrical, HVAC and duct work. The property was also structurally reinforced by a licensed engineer. NEW METAL ROOF installed 2023. There are SO many options and possibilities with the property and LOCATION!! NO RENTAL RESTRICTIONS and can be rented out daily! Keep the car parked and take a short walk to Downtown Dunedin with its unique restaurants, breweries, shoppes, farmers' market, marina and beautiful parks. Once there, you can hop on the Jolly Trolley for a unique way to visit the beaches and local attractions, or take the 37 mile long Pinellas Trail for those biking and athletic enthusiasts. Soak up all the Florida sun at nearby Famous Honeymoon Island and Caladesi Island State Park. This is an Excellent Location and Opportunity for those looking to live near all that Dunedin has to offer, or for those looking for a prime location to own an Investment property or Business/ Retail space!

757 Main Street, Dunedin

$624,900

3 Beds ⋅ 2 Baths ⋅ Oakland Sub SubDv. ⋅ 34698 Zip Code

This Key West Style Bungalow home is located within walking distance of Downtown Dunedin!! This 3 bed, 2 bath home underwent a complete renovation in 2020 including a new roof, windows, doors, and a/c. The home features an open-concept living with white shaker kitchen cabinets with quartz countertops and stainless steel appliances including a built-in wine refrigerator. The primary bedroom has a high ceiling with recessed lighting. The primary bath features a custom walk-in shower. The other bedrooms share a custom-designed bath with a tub and white tile. Vinyl planking flooring throughout with new ceramic tile in both bathrooms. All windows and doors are professionally trimmed and fitted with custom hardware. The fenced backyard is perfect for lounging or entertaining guests and has room for a pool. Walking distance to the Pinellas Trail which makes for an enjoyable bike ride to Downtown Dunedin. This community is golf cart friendly so jump on!! Dunedin is known for its breweries, restaurants, waterfront, shops, bars, farmer's markets, and year-round events. In addition, you can walk to a number of waterfront parks, Hammock Park, and Nature Preserve, or bike along the Dunedin Causeway to Honeymoon Island beach for a gorgeous Florida sunset.

721 Bay Street, Dunedin

$730,000

Oakland Sub SubDv. ⋅ 34698 Zip Code

MOTIVATED SELLER CHECK OUT THE PRICE DECREASE THIS IS YOUR CHANCE TO OWN AND DEVELOP PROPERTY AT THE ENTRANCE TO DOWNTOWN DUNEDIN. LOCATED AT THE CORNER OF MAIN STREET AND BASS BLVD. THERE IS NO REALTOR SIGN ON THIS PROPERTY. THE ADJACENT PARCELS ARE ALSO AVAILABLE, MLS # U8193737 (722 through 736 MAIN ST), ON SEPARATE CONTRACT. PLEASE DO NOT BOTHER TENANTS BUSINESS WHEN VIEWING. FRONTAGE ON MAIN STREET AND ON BASS BLVD. THE BUSINESS IS NOT FOR SALE. OWNER WILL CONSIDER OWNER FINANCING.

716 Main Street, Dunedin

$1,575,000

Oakland Sub SubDv. ⋅ 34698 Zip Code

Prime retail, office, medical, or mixed use property being offered. 13,930 sq ft included in three lots. 150 feet of frontage on Main Street in Dunedin (State Route 580). Two steel buildings, and one block building. 3216 sq ft, 1650 sq ft, and 1740 sq ft. Rear alley access. Both covered and open parking spaces. Property is currently a long operating used furniture store. All three lots and buildings must be purchased together. Also available for purchase is listing U8194172 ,716 Main St corner lot and buildings. Purchasing all three listings would provide 277 feet of Main Street frontage, with corner exposure at Bass Blvd.

722,726,732 Main Street, Dunedin

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