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$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

$495,000
4 Beds 2 Baths Harbor Heights Estates SubDv. 34695 Zip Code
Exceptional Safety Harbor pool home offering the upgrades, energy savings, and location buyers are looking for! Yes this is a great Home! Welcome to this beautifully updated 4-bedroom, 2-bath home in one of Safety Harbor’s most desirable neighborhoods. This move-in-ready property delivers the perfect Florida lifestyle with a resurfaced inground pool, screened lanai, and fully fenced backyard designed for relaxing, entertaining, and enjoying year-round outdoor living. Inside, you’ll find fresh interior and exterior paint, updated flooring throughout with no carpet, a renovated kitchen featuring granite countertops and modern finishes, and an updated primary bathroom. Major improvements provide peace of mind and efficiency, including hurricane-impact windows, a newer AC system, roof replacement in 2020, and owned solar panels keeping average electric costs around $35/month. Additional highlights include a spacious 2-car garage, non-flood zone location, and no HOA restrictions. Enjoy a golf-cart-friendly community just minutes from downtown Safety Harbor, Philippe Park, dining, shopping, community events, Tampa, airports, and Gulf beaches. A rare opportunity to own an energy-efficient pool home with significant upgrades in an unbeatable location — offering the lifestyle, savings, and convenience buyers are searching for.

2195 Glen Drive, Safety Harbor

$484,900
3 Beds 2 Baths Country Villas-Unit Two SubDv. 34695 Zip Code
You don’t want to miss this 3 bedroom, 2 bath, 2 car garage home in the much sought after Country Villas community in Safety Harbor. It is located on a quiet, peaceful cul-de-sac and is not in a flood zone, HIGH & DRY! This well cared for home offers many desirable updates. These include a new roof (2023), new AC (2022), new kitchen appliances (2020), some new kitchen cabinets (2021), new carpet in master bedroom, luxury vinyl in living area and other bedrooms (2020). The light and bright spacious open plan is designed for comfortable living, entertaining and includes a wood burning fireplace. This home offers a blend of tranquility and convenience being located near airports, restaurants, shopping and top rated schools. Minutes away is downtown Safety Harbor which provides great entertainment for the whole family. You will also have easy access to the world famous sandy beaches of the Gulf Coast. Next door is also available (112 Meadowcross), to set-up for perfect multi-generational living!

110 Meadowcross Drive, Safety Harbor

$494,900
3 Beds 2 Baths Country Villas-Unit Two SubDv. 34695 Zip Code
BRAND NEW LUXURY VINYL FLOORING INSTALLED THROUGHOUT! You don’t want to miss this 3 bedroom, 2 bath home tucked away in the very desirable Country Villas community in Safety Harbor. It is located at the end of a quiet peaceful cul-de-sac and not in a flood zone, HIGH & DRY! This well cared for home offers many desirable updates. These include a new roof and solar panel with Tesla Wall - for home energy storage (2025), new HVAC (2020), full kitchen update with soft close cabinets and bathrooms updated (2018). The spacious open plan is designed for comfortable living, entertaining and includes a wood burning fireplace. The home has hurricane rated windows and garage door as well as a whole house transfer switch for a generator. Step outside to a private, spacious backyard with plenty of room for a pool & beautiful fenced in dog run, with high quality artificial turf. This home offers a blend of tranquility and convenience being located near airports, restaurants, shopping and top rated schools. Minutes away is downtown Safety Harbor which provides great entertainment for the whole family. You will also have easy access to the world famous sandy beaches of the Gulf coast. Next door is also available (110 Meadowcross), to set-up for perfect multi-generational living!

112 Meadowcross Drive, Safety Harbor

$139,000
2 Beds 2 Baths Briar Creek Mobile Home Community Ii Condo SubDv. 34695 Zip Code
This 2 bedroom 2 bath with an office allows a cat or a dog up to 25 pounds. New HVAC unit installed on July 3/2026. The large open Living and dining rooms have laminate floors. Everything is very open with an island kitchen and family room with a skylight. There are 2 pantries and a storage closet in the kitchen. This home is 1354 square feet. There is also a side porch with windows & a storage shed with washer & dryer. You own the 52X75 lot included in the price. All you pay is $250 per month for maintenance fee which includes water, sewer, trash, lawn, private roads, clubhouse, heated pool & spa, gym, pickleball, and a lot where you can park your RV or your boat. This is a very friendly 55+ community with winding roads, little hills, lakes, and backs up to the bay. Room measurements approximate.

141 Forest Lane Unit 13, 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

$749,900
5 Beds 3 Baths De Soto Estates SubDv. 34695 Zip Code
This gorgeous pool home is truly captivating! Fully updated, it offers 5 bedrooms and 3 bathrooms, including two master suites on opposite sides of the house, each with private en-suites. The split-bedroom layout provides ample space for family or guests. The front door opens to a spacious Great Room that encompasses the living, dining, and kitchen areas. The updated kitchen features stainless steel appliances, granite countertops, and a charming coffee nook. Sliding glass doors lead to the pool deck, ideal for relaxing by the water. The fully fenced backyard includes a storage shed for extra convenience. Both master bedrooms have direct access to the pool deck and yard. The sparkling pool is oversized and always inviting. Currently listed on Airbnb, this property generates impressive returns. A circular driveway provides plenty of parking, and nearby Downtown Safety Harbor offers shopping, spas, restaurants, and breweries. Whether you keep it as a rental or make it your own, this Tampa Bay gem is a must-see. Philippe Park and Tampa Bay are just steps away with beautiful grounds and a boat launch, and flood insurance is NOT required. Don’t miss out—schedule a showing today!

2180 Philippe Parkway, Safety Harbor

$2,457,000
5 Beds 5 Baths Edge Water Reserve SubDv. 34695 Zip Code
Under Construction. The Showstopper at 3420 Channelside Ct - Completion is right around the corner for this premier custom waterfront home in Safety Harbor’s exclusive Edge Water Reserve. Meticulously designed by Grandview Custom Homes, this 5-bedroom, 5-bathroom architectural masterpiece offers 3,890 sq. ft. of living space on a quiet street of only six homes.Main Level Highlights:Grand Entrance: Soaring ceilings and a custom stairway with LED lighting and modern glass rails.Open Floorplan: Oversized custom porcelain tile flows into a luxurious kitchen and living space with coffered ceilings.Hidden Features: A massive pantry with a second refrigerator and a built-in desk/office area.Waterfront Lifestyle: Direct canal views with no rear neighbors, a custom swimming pool, and a fully equipped outdoor kitchen.Upper Level & Luxury Suites:Primary Suite Retreat: Features a private, large covered patio with magnificent views, dual walk-in closets, and a hidden safe room.Entertainment Hub: One of the four oversized upstairs bedrooms is designed as a Theater/Game Room, complete with its own mini bar.Premium Bathrooms: The primary bath showcases custom flooring, wall tile, an all-glass shower, and a freestanding tub.Structural & High-Tech Upgrades:Built for Safety: Hurricane-rated windows, foam insulation in the attic, and soundproofed interior walls.Tech-Ready: Includes a whole-house stereo system and is fully pre-wired for a home theater.Storage: An oversized 3-car garage with shelving and additional dedicated storage space.Experience the vibrant lifestyle of Safety Harbor, from the world-famous Safety Harbor Spa and Resort to the nearby award-winning beaches and Tampa International Airport.Would you like to schedule a private tour or see the latest interior progress photos?

3420 Channelside Court, 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

$1,750,000
4 Beds 4 Baths Bayfront Manor SubDv. 34695 Zip Code
Your dream home awaits in the heart of coveted Safety Harbor! This breathtaking waterfront estate offers the perfect blend of luxury, serenity, and modern living, with 4 bedrooms, 3.5 bathrooms, and an unbeatable 250 feet of frontage along the shimmering waters of Old Tampa Bay. Set on a lushly landscaped lot, this home is a masterpiece of design and functionality. From the moment you step through the grand double doors, you’re greeted by a soaring two-story foyer and a striking coastal-modern aesthetic. Sleek polished metal handrails and a glass banister set the tone for the impeccable style that flows throughout the home. Upstairs, the open-concept living spaces are bathed in natural light, thanks to floor-to-ceiling windows that frame jaw-dropping water views. The kitchen is a chef’s dream—boasting stone countertops, an oversized island, designer pendant lighting, high-end Bosch stainless appliances, and a dazzling backsplash of interlocking metal tiles. Here, every detail has been curated to impress. The nearly 700-square-foot primary suite is a retreat like no other, offering panoramic water views, a tranquil sitting area, and extra high ceilings. The spa-inspired en-suite bath features a modern soaking tub, an oversized walk-in shower, and dual vanities with stone counters. Beyond the bathroom, a show-stopping walk-in closet awaits, complete with custom shelving, a central island with display drawers, and even natural light from two windows. Two additional bedrooms on the main level are equally stylish and share a Jack-and-Jill bath, while a separate half bath and laundry room add convenience. Downstairs, the private in-law suite is a standout feature, complete with its own kitchen, living space, and direct access to the outdoors—perfect for extended family or guests. Step outside, and you’ll discover your personal paradise. A screened-in pool and spa with a sprawling pavered lanai offer multiple seating areas for relaxation or entertaining. The gazebo overlooking the bay creates an idyllic spot for morning coffee or sunset cocktails, while the private dock with water access is a dream for boaters and anglers alike. With over five garage spaces, there’s room for all your toys—whether it’s a boat, jet skis, or even a workshop. Located in a quiet, sought-after neighborhood minutes from downtown Safety Harbor, Philippe Park, and Clearwater’s world-class beaches and dining, this estate is more than a home—it’s a lifestyle. Don’t miss the chance to make every day feel like a vacation in this one-of-a-kind waterfront gem!

3484 Shore Drive, Safety Harbor

$1,999,999
5 Beds 4 Baths Washington-Brennan Sub SubDv. 34695 Zip Code
One or more photo(s) has been virtually staged. Experience your dream home in this thoughtfully designed, newly built, single family residence, in sought after Safety Harbor. Here, you'll live walking distance to downtown Safety Harbor and one block from the Bay. Experience numerous outdoor living areas and a third story terrace - your own private oasis! Inside you will be greeted with an open layout - the main floor has two bedrooms - a downstairs master, and a guest room or office - as you wish! Step into a kitchen with an oversized book-matched quartz island, large enough to fit the entire family. This area also has its own wine and bar room, flowing right outside to one of four private outdoor living areas - perfect for living and entertaining. Adorned with custom hard wood cabinets as well as Delta faucets and fixtures throughout, you'll be surrounded by quality. Enjoy plenty of natural light throughout the home via your brand-new hurricane impact rated windows. This house is a great size but yet still offers you a sizeable front and back yard with covered patios. The trees were purposefully maintained to provide ample shade to allow for residents and guests to enjoy Florida's outdoor lifestyle. Lot is pre-plumbed for you to add your own custom landscaping. You'll live and entertain here as the open kitchen area offers pass-through windows to entertain family and friends, maintaining a connection with the outdoors at each turn. Upstairs you'll find a second family room, theatre room, and three more bedrooms with high ceilings. Spacious closets, and a Jack and Jill bathroom await you here. A master with two walk-in closets, a double shower with body sprays, balcony, and more! Enjoy the convenience of a spacious second-floor laundry room with natural gas hookups. Relax on your back deck or walk upstairs to entertain guests on your very own, unique, sizeable, and private third story crow's nest! Here you can take in the water views of Tampa Bay or stargaze at night! This one-of-a-kind home offers instant equity as compared to new builds coming up in downtown Safety Harbor. Furthermore, buy this dream home with peace - it is up and out of a flood zone, and is built to stand - no issues at all during the recent hurricanes. Come by and take a look!

1045 Jesse Avenue, Safety Harbor