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2 Bedroom Homes for Sale in Dunedin Isles, Dunedin, FL

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Welcome to your dedicated resource for 2 bedroom homes for sale in Dunedin Isles, Dunedin, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Dunedin Isles, Dunedin, FL agents, Joseph Sullivan Real Estate specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 2 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 2 Bedroom Homes for Sale in Dunedin Isles, Dunedin, FL

1491 San Helen Dr, Dunedin
$550,000
2 Beds ⋅ 2 Baths ⋅ Dunedin Isles Estates 1st Add SubDv.
Welcome to easy Florida living with plenty of space to enjoy both indoors and out. This inviting home features a comfortable, light-filled layout with warm flooring, generous living and dining areas, and a spacious kitchen offering abundant cabinetry, ample counter space, and room for casual seating. Large windows throughout bring in natural light and offer views of the outdoor spaces. The bedrooms provide comfortable retreats, while the home also includes a dedicated laundry area for everyday convenience. Outside is where this property truly shines. Relax on the charming covered front porch, enjoy the screened patio for year-round outdoor living, or spend sunny Florida days beside the private screened-in pool. Beyond the pool area, additional patio and yard space surrounded by mature landscaping provides even more room to relax, entertain, or enjoy the outdoors. With multiple indoor and outdoor gathering spaces and a welcoming Florida feel, this home is ready for its next chapter.

1491 San Helen Dr, Dunedin
1559 Bayshore Boulevard, Dunedin
$425,000
2 Beds ⋅ 2 Baths ⋅ Dunedin Isles 1 SubDv.
Welcome to 1559 Bayshore Boulevard, where an incredible location, an oversized double lot, and endless possibilities come together in one of Dunedin’s most desirable areas! Situated on approximately 1/3 of an acre, this unique property offers an exceptional amount of outdoor space while placing you just steps from some of the best that Dunedin has to offer. Enjoy the ultimate Florida lifestyle with Sunset Park and the Pinellas Trail just moments away, while vibrant Downtown Dunedin and beautiful Honeymoon Island are both just a short distance from home. Whether you love biking the trail, catching a waterfront sunset, spending the day at the beach, or heading downtown for restaurants, breweries, shopping, festivals, and entertainment, this location puts it all within easy reach. The home features 2 bedrooms and 2 bathrooms with spacious living areas and a comfortable, functional layout. Outside is where this property really stands apart. The expansive double lot provides an incredible amount of room to enjoy today while offering exciting possibilities for the future. The fully fenced yard creates a private outdoor setting with plenty of space for entertaining, pets, gardening, or creating your own backyard oasis. Sports enthusiasts will love the half-court basketball court, which can also function as a full-size pickleball court, making the backyard perfect for recreation and entertaining. A one-car garage provides additional parking and storage. Properties offering this much land in such a sought-after Dunedin location are increasingly hard to find. Whether you’re looking for a charming home with an oversized yard, space to personalize and expand, or simply an incredible piece of property close to the water, trail, parks, beaches, and Downtown Dunedin, 1559 Bayshore Boulevard is packed with potential and ready for its next chapter!

1559 Bayshore Boulevard, Dunedin
1632 San Mateo Drive, Dunedin
$379,000
2 Beds ⋅ 2 Baths ⋅ Dunedin Isles 1 SubDv.
Virtually Staged. Some images shown have been virtually staged to illustrate the property’s potential. Furnishings and décor are not included. Welcome to 1632 San Mateo Drive, Dunedin, FL 34698, a charming vintage-style single-story home nestled along a quiet, tree-lined street less than one mile from the water, Pinellas county trail and downtown Dunedin. This inviting 2-bedroom, 2-bath residence blends classic Florida character with thoughtful updates and features a versatile Florida Room that provides 253 sq. ft. of additional space for a home office, den, guest area, or hobby room. Relax and enjoy Florida living from the screened lanai overlooking a private fenced backyard enhanced by stone walkways, a pergola, mature plantings, and plenty of space to unwind or entertain. Important improvements include an A/C system installed in 2020, updated double-pane windows, a tankless hot water heater, and the added convenience and peace of mind of a whole-house generator. The location truly sets this home apart, placing you close to Dunedin's waterfront lifestyle, local beaches, the Dunedin Causeway, Dunedin Golf Club, marinas, popular restaurants, shopping, and the many attractions that make Dunedin such a sought-after Gulf Coast destination. Whether enjoying a day near the water, exploring the surrounding community, or relaxing in your own backyard retreat, this home provides an appealing combination of character, convenience, and location. Schedule a tour today and experience everything 1632 San Mateo Drive has waiting for YOU!

1632 San Mateo Drive, Dunedin
1725 San Mateo Drive, Dunedin
$480,000
2 Beds ⋅ 3 Baths ⋅ Dunedin Isles 1 SubDv.
Welcome to 1725 San Mateo Drive, where timeless character, extensive updates, incredible outdoor living, and one of Dunedin’s most desirable locations come together! This charming 2-bedroom, 3-full-bath home with a one car garage is filled with personality and is perfectly positioned near Hammock Park, the Pinellas Trail, waterfront parks, Downtown Dunedin, and Honeymoon Island. From the moment you arrive, you’ll fall in love with the beautiful landscaping, adorable covered front porch, and inviting curb appeal. Step inside to discover original hardwood floors, charming arched openings, and a beautiful bay window that fills the home with natural light. These special architectural details give the home a warmth and character that simply can’t be recreated. Even better, this home combines its original charm with significant improvements throughout. Major updates include a 2022 roof, 2022 electrical updates, 2024 plumbing updates, 2021 HVAC system, 2017 water heater, 2026 insulation, and air ducts and vents updated in 2025—giving you the character of an established Dunedin home with many important improvements already completed. The kitchen opens directly to the large screened-in lanai, creating a seamless connection between the indoor and outdoor living spaces. Whether you’re enjoying morning coffee, hosting friends and family, or relaxing after a day at the beach, this expansive covered space is perfect for enjoying Florida living year-round. The primary bedroom features its own private bathroom as well as sliding glass doors leading directly to the beautiful deck and backyard. And what a backyard it is! Spacious, lush, and surrounded by mature landscaping, this outdoor retreat offers an incredible amount of room for entertaining, gardening, pets, outdoor dining, or simply relaxing beneath the Florida sunshine. Between the screened lanai, deck, front porch, and expansive yard, there are so many places to enjoy the outdoors. There is also an irrigation system! With two bedrooms and three full bathrooms, the floor plan offers flexibility and convenience rarely found in a home of this size. The location is truly exceptional. Hammock Park is just steps away, offering beautiful trails and natural surroundings, while the Pinellas Trail and waterfront parks are also nearby. Grab your bike or golf cart and head to Downtown Dunedin for locally owned restaurants, breweries, boutiques, festivals, farmers markets, and waterfront sunsets. When it’s time for the beach, Honeymoon Island is only about five minutes away! Adding even more peace of mind, the home experienced no water intrusion or storm damage during the recent hurricanes. With original hardwood floors, architectural charm, extensive updates, gorgeous outdoor living spaces, a spectacular backyard, and an unbeatable Dunedin location, 1725 San Mateo Drive offers the perfect combination of Old Florida character and the Dunedin lifestyle everyone loves.

1725 San Mateo Drive, Dunedin
1843 Pasadena Dr, Dunedin
$595,000
2 Beds ⋅ 2 Baths ⋅ Dunedin Isles 1 SubDv.
SOME HOMES ARE SIMPLY OWNED. OTHERS ARE LOVED, CULTIVATED AND ENJOYED FOR DECADES — AND 1843 PASADENA DRIVE IS ONE OF THOSE HOMES.... After 25 years of creating memories here, the longtime owners are ready to pass along this special slice of Dunedin.... Set on an oversized .28-acre lot along one of Dunedin Isles' classic brick streets, this 2 bedroom, 2 bath home offers 1,625 heated square feet plus an attached garage, brick-paver driveway and walkways, and an outdoor lifestyle that may just steal the show.... Step inside to a light and welcoming living room, separate dining area and beautifully updated kitchen featuring white Shaker-style cabinetry with soft-close and pull-out features, Cambria quartz countertops, stone backsplash and stainless appliances.... Beyond the kitchen, an expansive 25-foot family room has been the heart of countless gatherings, with plenty of room for hobbies, entertaining and the custom built-in bar where friends naturally seem to congregate.... Both bedrooms are generously sized, including a 15x12 primary bedroom, and the flexible floor plan offers comfortable everyday living with plenty of space to spread out.... NOW STEP OUTSIDE AND DISCOVER WHAT HAS MADE THIS HOME SO HARD FOR ITS OWNERS TO LEAVE.... A large covered and screened lanai flows into the heated saltwater pool and expansive screened pool deck, creating a true extension of the living space.... The pool was intentionally designed for relaxing and socializing, with a maximum depth of approximately 4½ feet, wide seating ledges, waterfall feature and whimsical dolphin mosaic.... A custom tiki bar, covered outdoor grilling area and additional spa create even more reasons to stay outside long after the sun goes down.... Beyond the screen enclosure, mature oak trees shade a remarkably spacious backyard with a storage shed and DIRECT ACCESS TO THE PINELLAS TRAIL.... The landscaping has been thoughtfully developed over many years to welcome butterflies, hummingbirds and other wildlife, with tropical palms and an extraordinary variety of flowering plants including hibiscus, pentas, coral honeysuckle, firebush, porterweed, jasmine and more.... The property has even been recognized as a Certified Wildlife Habitat, and the owners have documented 23 butterfly species in the yard over the years.... Located just a short walk from 90-acre Hammock Park and approximately 2 miles from the shops, restaurants, festivals and waterfront fun of Downtown Dunedin, with Dunedin Golf Course nearby and Honeymoon Island just a few miles away, this is a location made for enjoying everything that makes Dunedin special.... Major improvements include the 2019 roof plus extensive 2024 updates including HVAC, water heater, kitchen, appliances and flooring, with the pool enclosure rescreened in 2026.... COME WALK THE GARDENS, STEP OUT ON THE TRAIL, SIT UNDER THE OAKS AND EXPERIENCE THIS ONE FOR YOURSELF — THEN IMAGINE MAKING YOUR OWN MEMORIES HERE.... SCHEDULE YOUR PRIVATE SHOWING TODAY.

1843 Pasadena Dr, Dunedin
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