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$1,350,000

Welcome home to The Tupelo on 4th Cottage and Art Studio Property..... just behind the Gazebo! This iconic Safety Harbor property offers a blend of Historic and New with an incredible location in the heart of Safety Harbor! The charming 2-Story COTTAGE BUILDING (Approx 1,280 sq ft) fronting the 4th Ave N brick streets is a Wood-Frame Vernacular architecture structure featuring a wide front porch, wrap-around porch/Veranda, ADA Ramp/ Half Bathroom, and unique "fish scale" siding on the front gable - one of the most recognizable buildings in all of Safety Harbor. This historic property was maintained as a private residence until 2012 when it was converted in to Commercial use. For the last decade the front Cottage building as been used a LOCAL BOUTIQUE. The rear ART STUDIO BUILDING (Approx 840 sq ft) was built as an addition in 2014, and features separate entrance, 1 Office, Half Bath, Kitchenette area, high ceilings, Skylights and large open space. The two buildings are connected with an indoor hallway and also have separate entrances @ each end of the property. MOSAIC BENCH: The property is also home to a Custom 40-foot Mosaic Bench (with over 10,000 hand cut tiles!) inspired by Spanish Architect Antoni Gaudi'- a popular destination & photo location for Safety Harbor visitors. Myriad of Permitted and Conditional Uses offering flexibility and possibilities for this space: (MSM- Main Street Marketplace Zoning): Possible Uses: Residential, Multi-family, Art Gallery, Business and Professional Offices, Eating establishments/Taverns, Retail, Bed & Breakfast, etc. Buyers of this incredible property will enjoy the downtown lifestyle: 3rd Friday of every month (Evening Street Closure), Sip & Shop events, Sunday Markets next door at the Gazebo / 4th Ave N, July 4th & December Holiday Parades, and other Special Events. This unique property offers an amazing opportunity for the next Owner- please reach out for a private tour.

3 Beds ⋅ 2 Baths ⋅ Green Spgs SubDv. ⋅ 34695 Zip Code

Welcome home to The Tupelo on 4th Cottage and Art Studio Property..... just behind the Gazebo! This iconic Safety Harbor property offers a blend of Historic and New with an incredible location in the heart of Safety Harbor! The charming 2-Story COTTAGE BUILDING (Approx 1,280 sq ft) fronting the 4th Ave N brick streets is a Wood-Frame Vernacular architecture structure featuring a wide front porch, wrap-around porch/Veranda, ADA Ramp/ Half Bathroom, and unique "fish scale" siding on the front gable - one of the most recognizable buildings in all of Safety Harbor. This historic property was maintained as a private residence until 2012 when it was converted in to Commercial use. For the last decade the front Cottage building as been used a LOCAL BOUTIQUE. The rear ART STUDIO BUILDING (Approx 840 sq ft) was built as an addition in 2014, and features separate entrance, 1 Office, Half Bath, Kitchenette area, high ceilings, Skylights and large open space. The two buildings are connected with an indoor hallway and also have separate entrances @ each end of the property. MOSAIC BENCH: The property is also home to a Custom 40-foot Mosaic Bench (with over 10,000 hand cut tiles!) inspired by Spanish Architect Antoni Gaudi'- a popular destination & photo location for Safety Harbor visitors. Myriad of Permitted and Conditional Uses offering flexibility and possibilities for this space: (MSM- Main Street Marketplace Zoning): Possible Uses: Residential, Multi-family, Art Gallery, Business and Professional Offices, Eating establishments/Taverns, Retail, Bed & Breakfast, etc. Buyers of this incredible property will enjoy the downtown lifestyle: 3rd Friday of every month (Evening Street Closure), Sip & Shop events, Sunday Markets next door at the Gazebo / 4th Ave N, July 4th & December Holiday Parades, and other Special Events. This unique property offers an amazing opportunity for the next Owner- please reach out for a private tour.

135 4th Avenue N, Safety Harbor

$399,000

Welcome to the Sunshine Cottage—a beautifully restored and fully furnished 2-bedroom, 1-bath retreat just four blocks from Main Street in Safety Harbor. Blending vintage charm with modern comfort, this 1948 cottage is filled with warmth, character, and natural light, offering a truly unique living experience in one of Tampa Bay’s most beloved coastal towns. Currently operating as a successful Airbnb with a five-star Superhost history, this property presents a rare opportunity for immediate income generation or a seamless transition into a private residence. Whether you’re an investor, seasonal buyer, or someone seeking a creative escape, the flexibility here is unmatched. Inside, you’ll find a bright, open layout with high ceilings and thoughtfully curated finishes throughout. The kitchen features a colorful mosaic backsplash, abundant cabinetry, and flows effortlessly into the main living space—perfect for entertaining. The home’s two bedrooms are cozy and inviting, including a primary with a queen bed and a guest room with a trundle, ideal for visitors. The updated bathroom showcases a modern white vanity, honeycomb tile flooring, and a beautifully tiled shower. Step outside to enjoy the charming front porch and private patio—perfect spaces to unwind and soak in the Florida sunshine. Situated on a spacious lot with a durable metal roof, the home offers both character and peace of mind. Just moments away, downtown Safety Harbor offers an unmatched lifestyle—Sunday markets, live music, waterfront views, and local favorites, along with easy access to Philippe Park, scenic bike trails, and the bay. Whether you’re looking for a turnkey investment, a weekend getaway, or a full-time residence with soul, Sunshine Cottage delivers a rare blend of charm, location, and opportunity. There is also a unique opportunity to own multiple homes with 3 total parcels (17,250 sq ft total) on the same block.

2 Beds ⋅ 1 Baths ⋅ Spring Park Rev SubDv. ⋅ 34695 Zip Code

Welcome to the Sunshine Cottage—a beautifully restored and fully furnished 2-bedroom, 1-bath retreat just four blocks from Main Street in Safety Harbor. Blending vintage charm with modern comfort, this 1948 cottage is filled with warmth, character, and natural light, offering a truly unique living experience in one of Tampa Bay’s most beloved coastal towns. Currently operating as a successful Airbnb with a five-star Superhost history, this property presents a rare opportunity for immediate income generation or a seamless transition into a private residence. Whether you’re an investor, seasonal buyer, or someone seeking a creative escape, the flexibility here is unmatched. Inside, you’ll find a bright, open layout with high ceilings and thoughtfully curated finishes throughout. The kitchen features a colorful mosaic backsplash, abundant cabinetry, and flows effortlessly into the main living space—perfect for entertaining. The home’s two bedrooms are cozy and inviting, including a primary with a queen bed and a guest room with a trundle, ideal for visitors. The updated bathroom showcases a modern white vanity, honeycomb tile flooring, and a beautifully tiled shower. Step outside to enjoy the charming front porch and private patio—perfect spaces to unwind and soak in the Florida sunshine. Situated on a spacious lot with a durable metal roof, the home offers both character and peace of mind. Just moments away, downtown Safety Harbor offers an unmatched lifestyle—Sunday markets, live music, waterfront views, and local favorites, along with easy access to Philippe Park, scenic bike trails, and the bay. Whether you’re looking for a turnkey investment, a weekend getaway, or a full-time residence with soul, Sunshine Cottage delivers a rare blend of charm, location, and opportunity. There is also a unique opportunity to own multiple homes with 3 total parcels (17,250 sq ft total) on the same block.

526 5th Avenue N, Safety Harbor

$899,000

NO FLOOD ZONE. Rare opportunity just steps from downtown Safety Harbor on the coveted cobblestone stretch of 5th Avenue. Originally built in 1925 during the height of the Sears & Roebuck catalog home era, this classic American Foursquare features the enduring craftsmanship of early 20th-century construction, including dense old-growth lumber known for its exceptional strength and longevity. While thousands of these homes were built nationwide, only a limited number of comparable early 20th-century homes remain in Florida today. Featuring tall ceilings uncommon for homes of this era, the property offers a unique sense of openness and character throughout. Spanning over 2,700 square feet across three levels, the home offers 4 bedrooms, 3 bathrooms, bonus/flex spaces, a loft, and a layout ideal for buyers seeking something distinctive and full of personality. The primary suite features a private balcony, dual walk in cloests and a remodeled bathroom retreat. Inside, you’ll find an open kitchen with an island, dedicated laundry room, elegant laminate flooring, and a wood-burning fireplace with a chimney that adds warmth and historic charm to the living space. Flexible living areas throughout the home provide endless possibilities for guest space, offices, creative studios, or additional entertaining areas. Outside, a welcoming back patio overlooks the spacious backyard, offering endless potential to create your own outdoor retreat, whether it’s a garden, entertaining space, or future vision. A long-lasting metal roof adds additional value and peace of mind, while the cobblestone street setting enhances the home’s undeniable charm and sense of arrival. Walkable homes this close to downtown Safety Harbor are exceptionally rare. Just four blocks from restaurants, coffee shops, the pier, live music, art festivals, boutiques, Third Friday celebrations, and the world-famous Safety Harbor Spa. Whether you’re looking to restore, personalize, invest, or simply own a truly distinctive property in one of Tampa Bay’s most beloved waterfront towns, opportunities like this rarely come available.

4 Beds ⋅ 3 Baths ⋅ Spring Park Rev SubDv. ⋅ 34695 Zip Code

NO FLOOD ZONE. Rare opportunity just steps from downtown Safety Harbor on the coveted cobblestone stretch of 5th Avenue. Originally built in 1925 during the height of the Sears & Roebuck catalog home era, this classic American Foursquare features the enduring craftsmanship of early 20th-century construction, including dense old-growth lumber known for its exceptional strength and longevity. While thousands of these homes were built nationwide, only a limited number of comparable early 20th-century homes remain in Florida today. Featuring tall ceilings uncommon for homes of this era, the property offers a unique sense of openness and character throughout. Spanning over 2,700 square feet across three levels, the home offers 4 bedrooms, 3 bathrooms, bonus/flex spaces, a loft, and a layout ideal for buyers seeking something distinctive and full of personality. The primary suite features a private balcony, dual walk in cloests and a remodeled bathroom retreat. Inside, you’ll find an open kitchen with an island, dedicated laundry room, elegant laminate flooring, and a wood-burning fireplace with a chimney that adds warmth and historic charm to the living space. Flexible living areas throughout the home provide endless possibilities for guest space, offices, creative studios, or additional entertaining areas. Outside, a welcoming back patio overlooks the spacious backyard, offering endless potential to create your own outdoor retreat, whether it’s a garden, entertaining space, or future vision. A long-lasting metal roof adds additional value and peace of mind, while the cobblestone street setting enhances the home’s undeniable charm and sense of arrival. Walkable homes this close to downtown Safety Harbor are exceptionally rare. Just four blocks from restaurants, coffee shops, the pier, live music, art festivals, boutiques, Third Friday celebrations, and the world-famous Safety Harbor Spa. Whether you’re looking to restore, personalize, invest, or simply own a truly distinctive property in one of Tampa Bay’s most beloved waterfront towns, opportunities like this rarely come available.

516 5th Avenue N, Safety Harbor