Safety Harbor FL Historical Real Estate, Homes for Sale

3 Beds ⋅ 2 Baths ⋅ Espiritu Santo Spgs SubDv. ⋅ 34695 Zip Code

LOCATION, LOCATION, LOCATION! Rare opportunity to own a multi-family property in the heart of beautiful downtown Safety Harbor! Welcome to one of Safety Harbor’s most desirable brick-lined streets, where charming small-town character meets the best of the Florida lifestyle. Just steps from the waterfront, this unique two-story property offers two separate living units, strong rental potential, a spacious lot, and an unbeatable walk-to-downtown location. The first-floor unit features a welcoming kitchen, living room, dining area, two bedrooms plus an office, and rents for approximately $2,100 month. Upstairs, the second unit offers a kitchen, living room, one bedroom and one bathroom, currently renting for approximately $1,450 month. Each unit has its own electric meter, while the landlord currently pays water, sewer, and trash, totaling approximately $200 month. A shared laundry room is conveniently located on the backside of the property. The expansive lot provides plenty of outdoor space and even offers back alley access, with the potential for a future owner to install a pool, double gate for added convenience. The possibilities are exciting—continue using the property as an income-producing multi-family investment, make it your own and live in one unit while renting the other, convert it back to a single-family residence, or explore the potential for a brand-new home on the generous lot. And then there’s the location. Walk to Safety Harbor’s charming Main Street, local restaurants, boutique shops, festivals, the Safety Harbor Marina, Philippe Park, and the iconic Safety Harbor Resort & Spa. The waterfront is just at the end of the street, offering beautiful Tampa Bay sunrises and that unmistakable coastal Florida lifestyle. When it’s time for a beach day, Clearwater Beach and Honeymoon Island are just a short drive away. NO HOA. NOT IN A FLOOD ZONE. Selling AS-IS. Whether you're looking for an investment property, a unique multi-generational opportunity, or a property with redevelopment potential in one of Pinellas County’s most sought-after communities, this is an opportunity you won't want to miss. Live right in the heart of Safety Harbor!

245 Tucker Street, Safety Harbor

$399,000

3 Beds ⋅ 2 Baths ⋅ Lincoln Highlands SubDv. ⋅ 34695 Zip Code

Welcome to this charming 3-bedroom, 2-bathroom home in desirable Safety Harbor! Offering approximately 1,125 square feet of living space, this property presents an excellent opportunity for a primary residence or investment. Features include laminate flooring throughout, a 2024 HVAC system, a water heater, and a functional layout designed for comfortable living. Conveniently located near vibrant downtown Safety Harbor, restaurants, shopping, parks, waterfront attractions, and major roadways. With its sought-after location, versatility, and income-producing potential, this home is ready for its next chapter. Schedule your private showing today!

675 11th Place, Safety Harbor

$650,000

6 Beds ⋅ 2 Baths ⋅ Youngbloods J J Add SubDv. ⋅ 34695 Zip Code

Great investment opportunity. Beautiful Safety Harbor Duplex. Separate utilities for each unit. Tenants pay all utilities. Low maintenance with all tile floors, fenced yard. Rear unit updated and occupied, tenant is months to month. Parking for two cars each unit. Lots of newer homes in neighborhood. Walking distance to town.

420 Maple Way, Safety Harbor

$309,000

4 Beds ⋅ 2 Baths ⋅ Lincoln Highlands Rep SubDv. ⋅ 34695 Zip Code

Under contract-accepting backup offers. Virtually Staged. This well-maintained 4-bedroom, 2-bath single-family home offers generous space both inside and out—perfect for a comfortable lifestyle or investment opportunity. Ideally located less than half a mile from downtown Safety Harbor, this property puts you steps from vibrant restaurants, parks, special events, and stunning Tampa Bay views from the brand-new Safety Harbor pier. The open living and kitchen area creates a bright, welcoming environment ideal for gatherings, while the split floorplan ensures privacy when it’s time to unwind. Fresh interior paint and updated bathroom fixtures make this home move-in ready and easy to personalize. Out back, enjoy a fully fenced, spacious yard—perfect for pets, play, gardening, or future outdoor enhancements. A convenient storage shed provides extra room for tools, toys, and seasonal items. With close proximity to top-rated schools, community parks, and all the charm of downtown Safety Harbor, this home delivers lifestyle, convenience, and long-term value.

1120 6th Street N, Safety Harbor

$430,000

3 Beds ⋅ 2 Baths ⋅ Palm View Terrace SubDv. ⋅ 34695 Zip Code

Pool home in Safety Harbor for under 431k!!! Loads of charm, a lot of backyard, and a pool to top it all off—this Safety Harbor gem has plenty to love! Tucked away on a brick-lined street, this 3-bedroom, 2-bath home welcomes you with a bright, open living room, a nicely updated kitchen, and a flexible bonus/dining/family room that makes everyday living easy. The spacious primary bedroom offers two closets and an attached bathroom. There are two additional bedrooms and a second bathroom. Out back, the generously sized fully fenced yard gives you the best of both worlds: a sparkling pool for sunny afternoons and plenty of grassy space to play, entertain, or simply unwind. This one has a BRAND NEW ROOF! Located in a prime location close to Philippe Park, Safety Harbor Spa and just a short walk to Main St with all the shops, restaurants, and their monthly 3rd Friday events. With so much character, space, and outdoor appeal, this one is a true Safety Harbor charmer!

615 5th Avenue N, Safety Harbor

$519,000

4 Beds ⋅ 2 Baths ⋅ Seminole Park Rev SubDv. ⋅ 34695 Zip Code

Virtually Staged. What a stunning home and the location in DOWNTOWN SAFETY HARBOR is superb! You can WALK TO MAIN STREET IN JUST 3 MINUTES! This excellent floor plan has 4 bedrooms PLUS A BONUS ROOM/OFFICE/DEN AREA and 2 FULL REMODELED bathrooms. There is NO CARPET, JUST BEAUTIFUL LUXURY VINYL FLOORING. Enjoy the split floor plan with a PRIVATE MASTER SUITE retreat on one side of the house. There is a bedroom and additional room for an office, work out room or private sitting area. The SHOWER IS HANDICAP ACCESSIBLE WITH A ZERO ENTRY. The KITCHEN IS GORGEOUS with a GAS STOVE, fabulous high end GRANITE COUNTERTOPS, NEWER CABINETS and an abundance of cabinets and storage. Countertop seating is a great option with the expansive space of the renovated dream kitchen. How about the yard, wow! It's a BACKYARD OASIS WITH ALMOST A QUARTER OF AN ACRE, FENCED IN, STORAGE CLOSET AND A RELAXING SEATING AREA. The outdoor furniture will stay with the house. There is a kitchenette in the garage with a mini split as well as lots of storage and ROOM TO PARK A CAR. NEW ROOF IN 2020 AND NEW AC IN 2024, UPDATED WINDOWS, NO FLOOD ZONE! Don't forget about Third Friday, fabulous restaurants, shoppings, spa, fun bars, library, Philippe Park and the rec center. Enjoy all that Safety Harbor has to offer in this centrally located, well appointed home!

375 10th Avenue N, Safety Harbor

$499,900

5 Beds ⋅ 2 Baths ⋅ Na SubDv. ⋅ 34695 Zip Code

Handyman special, 5 bedroom, 2 bath home very close to downtown Safety Harbor. This property is a sturdy masonry home in a non-flood area with an additional buildable lot, all fenced in and great for pets.

2157 Railroad Avenue, Safety Harbor

$425,000

3 Beds ⋅ 2 Baths ⋅ Unplatted SubDv. ⋅ 34695 Zip Code

Under contract-accepting backup offers. UNDER CONTRACT- ACCEPTING BACK UP OFFERS. Completely renovated from top to bottom, this stunning block home with fully fenced in backyard offers the perfect combination of modern style and long-term peace of mind. Every major improvement has been completed through a fully permitted renovation, including a new roof, complete electrical rewire, new windows, new HVAC system, new ductwork, and numerous additional upgrades throughout the home. The thoughtfully updated interior features a bright, open layout with quality finishes, creating a truly move-in-ready home where everything has already been done for you. Located in Flood Zone X, flood insurance is typically not required by lenders. Beyond the home itself, you’ll love the unbeatable location. Situated just 5 minutes from charming Downtown Safety Harbor, you’ll have easy access to award-winning restaurants, local boutiques, waterfront parks, the Safety Harbor Marina, year-round festivals, and the world-renowned Safety Harbor Resort & Spa. With convenient access to Tampa, Clearwater, beautiful Gulf beaches, and both Tampa International and St. Pete-Clearwater airports, this home offers the perfect blend of small-town charm and everyday convenience. Some photos have been virtually enhanced using AI for illustrative purposes only.

595 Pine Street, Safety Harbor

$1,350,000

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

$699,900

3 Beds ⋅ 2 Baths ⋅ Harbor Hill Park SubDv. ⋅ 34695 Zip Code

REDUCED!! Beautiful Safety Harbor 3 Bedroom, 2 Bath, 4 car garage, pool home situated on a double lot! Large open, updated eat-in kitchen, with convenient adjoining office area. Screened porch leading to the pool, spa and covered deck. Included is a large, stand-alone 35 x 25 back yard garage/workshop. The World-Renowned Safety Harbor Spa & Resort is just a quick drive, walk, or bike ride away, along with bustling Main Street offering quality restaurants, unique shops & vibrant pubs. Walk & bike along beautiful Bayshore Blvd, on your way to top-rated Philippe Park. Meet your neighbors & local business owners each Third Friday Main Street party and various festivals throughout the year. Safety Harbor has several dog parks and recreation centers with activities for all ages. For the boating enthusiast, Safety Harbor Marina, Cooper's Bayou & Philippe Park are your quick access to beautiful Tampa Bay, as well as entrance to the bay for your kayak or canoe! A quick drive and you are at world class Clearwater Beach or across the Courtney Campbell takes you to Tampa Airport & Tampa! Golf cart friendly area!

915 Harbor Hill Drive, Safety Harbor

$439,900

3 Beds ⋅ 2 Baths ⋅ Oak Haven Estates SubDv. ⋅ 34695 Zip Code

Under contract-accepting backup offers. Virtually Staged. (3rd bedroom/ flex room ) Welcome to this beautifully updated 3-bedroom, 2-bath home tucked away in one of Safety Harbor's most desirable neighborhoods. High and dry with no required flood insurance and no HOA, this move-in ready home offers the perfect blend of modern updates, flexible living spaces, and an unbeatable location just minutes from vibrant downtown Safety Harbor. Step inside to discover an inviting open-concept floor plan where engineered hardwood flooring, updated trim, abundant natural light, and neutral finishes create a warm, contemporary feel. The spacious living, dining, and kitchen areas flow seamlessly together, making everyday living and entertaining effortless. The kitchen features a Samsung appliance package that conveys with the home, including a 5-burner gas range, gas convection oven, and French-door refrigerator, making it ideal for both everyday cooking and entertaining. A versatile flex room currently serves as the third bedroom, offering endless possibilities as a guest suite, home office, playroom, fitness room, or media space to fit your lifestyle. Major improvements have already been completed, including a durable metal roof, hurricane-impact windows, upgraded 200-amp electrical service, new HVAC ductwork and registers, and beautifully updated bathrooms, providing peace of mind for years to come. Step outside and discover where this home truly shines. Relax year-round in the screened lanai or host family and friends beneath the expansive covered patio surrounded by mature oak trees. The fully fenced backyard offers plenty of room for pets, gardening, or future outdoor enhancements, while the air-conditioned workshop is perfect for hobbies, a creative studio, remote work, or additional storage. Whether you're taking your golf cart to downtown Safety Harbor for dinner, spending the afternoon at Philippe Park, or simply relaxing beneath the canopy of mature oaks in your own backyard, this home offers the Florida lifestyle buyers dream about. Move-in ready and thoughtfully updated, this is a rare opportunity to enjoy everything that makes Safety Harbor one of Tampa Bay's most sought-after communities. Select photos have been virtually staged.

1412 Oak Haven Drive, Safety Harbor

$1,350,000

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 back 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 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 local customer base + increased Visitors and foot traffic on Safety Harbor Special events such as: 3rd Friday of every month (Evening Street Closure), Sip & Shop event, 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

$3,245,000

West Green Spgs SubDv. ⋅ 34695 Zip Code

Rare full-block assemblage in the heart of Safety Harbor — Block 24, Lots 7-11, spanning the complete block face on 2nd St N from 6th Ave to 5th Ave, one block north of Main Street, offered as a 5-parcel package (37,700 SF / 0.87 acres). Two livable homes and three redevelopment lots steps from Main Street Dining, Safety Harbor Resort & Spa, Waterfront Park, and Marina. Two homes may be available for seller leaseback during permitting. Property is available as a complete package or individually — seller is open to selling lots in smaller groupings, giving buyers the flexibility to right-size their acquisition. The property can be sold individually or as a package, with other ML#'s, addresses and parcel IDs being noted in the Realtor Only Remarks. Whether targeting one lot, two, or three, this corridor warrants a conversation.

515 2nd Street N, Safety Harbor

$3,245,000

2 Beds ⋅ 1 Baths ⋅ West Green Spgs SubDv. ⋅ 34695 Zip Code

Rare full-block assemblage in the heart of Safety Harbor — Block 24, Lots 7-11, spanning the complete block face on 2nd St N from 6th Ave to 5th Ave, one block north of Main Street, offered as a 5-parcel package (37,700 SF / 0.87 acres). Two livable homes and three redevelopment lots steps from Main Street Dining, Safety Harbor Resort & Spa, Waterfront Park, and Marina. Two homes may be available for seller leaseback during permitting. Property is available as a complete package or individually — seller is open to selling lots in smaller groupings, giving buyers the flexibility to right-size their acquisition. The property can be sold individually or as a package, with other ML#'s, addresses and parcel IDs being noted in the Realtor Only Remarks. Whether targeting one lot, two, or three, this corridor warrants a conversation.

515 2nd Street N, Safety Harbor

$1,299,000

Green Spgs SubDv. ⋅ 34695 Zip Code

We are proud to present 108 4th Avenue South, a well-located professional office building just steps from Main Street in the heart of downtown Safety Harbor. Positioned in one of Tampa Bay’s most desirable and walkable submarkets, this property offers a rare opportunity for an owner-user or investor to acquire a highly functional office asset in a nationally recognized small-town setting. Constructed in 1957, the 3,812 SF building sits on approximately 0.16 acres and is located in Flood Zone X. The property is currently configured as a medical office, featuring a welcoming front waiting area and reception desk, ten private offices, a dedicated conference room, three restrooms, and a kitchen. The efficient layout provides flexibility for a variety of professional uses, including medical, legal, financial, counseling, or general office operations. For additional information, please review the floor plan. The building benefits from two primary entrances on the east and west sides of the property, allowing for convenient access, potential tenant separation, or functional flow for staff and clients. Excellent office sizes and a practical floor plan contribute to the property’s overall usability and long-term adaptability. Just off Main Street, the location offers exceptional visibility and immediate proximity to Safety Harbor’s restaurants, boutiques, breweries, waterfront parks, and community amenities. The property is also steps away from the lively Third Friday Street Festival, a monthly celebration of music, art, food, and local culture that draws consistent foot traffic and reinforces the area’s vibrant atmosphere. Safety Harbor has recently been recognized by USA Today as the #10 Best Main Street in the United States and the #5 Best Small Town in the South, underscoring the strength of the local market and the long-term appeal of downtown ownership. Whether utilized as a professional office, medical practice, or boutique business headquarters, 108 4th Avenue South offers a compelling combination of location, functionality, and community presence in one of Florida’s most charming coastal towns.

108 4th Avenue S, Safety Harbor

$499,900

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

Casa del Tren — Renovated Cottage on a Rare Downtown Lot That Pays Its Own Way It's rare to find a lot like this so close to everything: an oversized 50x140 parcel with mature trees, privacy, and room to imagine, minutes from the shops, restaurants, parks, and waterfront of Downtown Safety Harbor. And the home that sits on it lives up to the setting, a beautifully renovated classic Florida cottage, professionally updated and thoughtfully decorated, with a bright, open great-room layout that feels like home the moment you enter. A top-rated elementary school sits just two blocks away. Out back, a privately fenced and lighted paver courtyard offers shade and seclusion just off Main Street, a favorite with pet owners and an easy place to unwind. With space to garden, expand, or simply breathe, the lot is the kind of rarity that's almost impossible to find this close to downtown. It offers real peace of mind, too: set in low-risk FEMA Flood Zone X and the safer Evacuation Zone D, it has never flooded, evacuated, or sustained storm damage in eight years. Here's what makes Casa del Tren truly special: it's a wonderful home that can also pay its way, entirely on your terms. Live in it full-time, keep it as a winter retreat, or let it earn when you're away. For eight years it has quietly thrived as one of Safety Harbor's most-loved vacation rentals, with hundreds of 5-star reviews, a loyal following, and an established brand, website, and online presence. The proven income engine is here if you want it, and no obligation if you don't. It's offered fully furnished and rental-ready, so you can step into a turnkey operation from day one, or simply make it your own. There's no HOA and no special permitting hurdle to rent it, and detailed financials are available on request. Casa del Tren has been lovingly run by the owners under their "Stay in the South" brand, a small collection of hospitality-driven homes known for meticulous care. That same attention to detail earned their Nashville property, the Heidtke House, a feature on the international travel series "Sense of Place." Now ready to slow down, they're passing this one on in turnkey condition to its next owner. This is a rare opportunity to purchase in one of the most sought after areas in Downtown Safety Harbor.

839 3rd Street N, Safety Harbor

$3,999,000

Green Spgs SubDv. ⋅ 34695 Zip Code

We are proud to exclusively market for sale Harbor Inn on Main, a rare generational asset located in the heart of one of America's most celebrated small towns. With 155 feet of frontage on vibrant Main Street—recently ranked #10 Best Main Street in the U.S. and #5 Best Small Town in the South by USA Today—this mixed-use property offers unmatched charm, versatility, and income potential. Built in 1918 and meticulously maintained, the property features 9,605 SF under roof and 2,599 SF of balcony space. Zoned Main Street Marketplace (MSM), this historic gem supports a wide variety of permitted uses including retail, multi-family, office, hospitality, and entertainment. Currently operating as a hybrid LTR/STR top-rated Airbnb Superhost with (8) turnkey apartment units—(6) one-bedrooms and (2) studios—each with full kitchens and baths. This income-generating property is perfect for investors or owner-occupiers. An opportunity also exists to expand with a 9th additional unit or owner/manager’s suite. The ground-floor retail space is elevated above street level and flooded with natural light, offering excellent visibility and a welcoming Main Street presence. Total retail square footage is equal to 2,983 SF and is currently rented month to month offering flexibility for an owner operator to occupy or generate longer term income. Recent capital improvements include a new roof (2020) on the primary building and new HVAC with ductwork (2023) in the retail space. Additional highlights: 14 private parking spaces, Garage/storage space, Located in Flood Zone X, Just blocks from the iconic Safety Harbor Spa, Two majestic “Great Oaks” on site, Steps away from the lively Third Friday Street Festival—a monthly downtown celebration of music, art, food, and community. This is more than a property—it’s a piece of Safety Harbor history with modern upside. Contact us today for details or to schedule a private tour.

454 Main Street, Safety Harbor

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