Safety Harbor Homes with Two Story Style

This unique property offers endless possibilities, nestled on a private, secluded .63-acre lot with no community deed restrictions. A true one-of-a-kind opportunity, the property features a spacious main home, an OVERSIZED DETACHED GARAGE WITH ADDITIONAL LIVING QUARTERS (approximately 600sqft not included in listed square footage), multiple covered outdoor spaces, plenty of parking, and a large private backyard. The main home offers 4 bedrooms, 2 full bathrooms, and 1 half bath. The main floor features an inviting open gathering area with living and dining spaces that flow into the spacious kitchen. Luxury vinyl flooring, neutral paint colors, and recessed lighting create a fresh, modern feel throughout. The kitchen is designed for entertaining and features white shaker-style soft-close cabinets, stainless steel appliances, a farmhouse-style backsplash, range hood, and apron-front sink. The light-filled primary suite is conveniently located on the main floor and includes a built-in dressing table and ensuite bathroom. The ensuite features dual sinks and a floor-to-ceiling tiled walk-in shower with glass doors. A half bath and laundry area are also located on the first floor. From the downstairs living area enjoy access to the large, covered patio area with space to enjoy year-round. This fenced patio features a ceiling fan and low-maintenance artificial turf. Upstairs, you'll find 3 additional bedrooms, a full bathroom, a large living area with fireplace, a spacious storage closet, and another covered screened porch—perfect for relaxing, enjoying the breeze, or stargazing. The second-floor living area features luxury vinyl flooring, neutral paint, a built-in bookcase, and stunning stained-wood plank ceilings that add warmth and character. The oversized detached garage features two oversized garage doors and epoxy flooring, offering incredible flexibility for storage, a workshop, gym, or hobbies. A covered breezeway connects the garage to the main home. Adjacent to the garage is an approximately 600-square-foot mother-in-law quarters, complete with a kitchenette, full bathroom, living area, and 2 bedrooms—ideal for guests, extended family, a home office, or additional living space. The expansive backyard provides even more room to enjoy the Florida lifestyle, with another large covered patio perfect for quiet barbecues or gatherings with family and friends. Additional features include an outdoor fire pit, gardening space, basketball hoop, and plenty of parking. 2018 main roof, 2021 garage/mother-in-law quarters roof, and 2026 main-home water heater. Enjoy the best of Safety Harbor with a quick golf-cart ride to downtown, parks, the Safety Harbor Recreation Center, restaurants, and local attractions. Unique properties like this are hard to find. Endless possibilities, exceptional space, and a prime Safety Harbor location—welcome home!

1120 1st Avenue N, Safety Harbor

$739,900

4 Beds ⋅ 2 Baths ⋅ TB8533653 MLS

Welcome home where modern updates, exceptional living space, and an unbeatable Safety Harbor location come together in one remarkable home. Nestled on an oversized 0.28-acre lot in the desirable Winding Oaks community, this beautifully updated 4-bedroom, 2-bath residence offers a true 2,782 square feet of living space, including a fully finished, air-conditioned walkout basement connected to the main level by a striking spiral staircase. Step inside to discover a spacious, open-concept floor plan filled with natural light and designed for both everyday living and entertaining. The heart of the home is the stunning, updated kitchen featuring an oversized granite island, abundant cabinetry, granite countertops, stainless steel appliances, and an expansive breakfast bar overlooking the inviting family room with its impressive stone wood-burning fireplace. Luxury vinyl plank flooring installed throughout the home in 2023 creates a seamless, contemporary look while adding durability and warmth. The thoughtfully updated kitchen includes new granite countertops, refrigerator, range, microwave, dishwasher, garbage disposal, and additional upgrades completed in 2023, making it truly move-in ready. Both bathrooms also feature matching granite countertops, providing a cohesive and upscale finish throughout the home. One of the home's most unique features is the 740-square-foot finished walkout basement, offering incredible flexibility as a fourth bedroom, guest suite, home office, media room, fitness area, playroom, or multigenerational living space. An additional oversized storage room serves as the closet for the fourth bedroom and provides abundant space rarely found in homes throughout the area. The spacious primary suite offers privacy and comfort, while the secondary bedrooms are generously sized with excellent natural light. Every room reflects the pride of ownership and extensive updates completed over the past several years. Outdoor living is equally impressive. Step outside to the expansive screened-in covered deck, creating an incredible extension of the living space and the perfect setting for morning coffee, outdoor dining, or relaxing while overlooking the very large fenced backyard. The irrigation system is supplied by a private well featuring a brand-new deep well pump installed in July 2026, helping maintain the lush landscaping while reducing water costs. Additional recent improvements include: • New downstairs AC (2026) • New upstairs AC (2023) • New roof (2015) • Luxury vinyl plank flooring (2023) • Granite countertops throughout (2023) • New refrigerator, range, microwave, dishwasher, and garbage disposal (2023) Location is everything, and this home delivers. Enjoy the convenience of being walking or golf-cart distance to charming downtown Safety Harbor, with its award-winning restaurants, boutiques, festivals, marina, and waterfront parks. You're also just one mile from the iconic Safety Harbor Pier and only moments from the Safety Harbor Community Center, waterfront parks, top-rated schools, Philippe Park, Tampa International Airport, beautiful Gulf beaches, and major commuter routes. With extensive updates, an exceptionally rare finished basement, an oversized lot, an incredible outdoor living space, and one of the most desirable locations in Pinellas County, this home offers a lifestyle that is truly difficult to duplicate. This is your opportunity to own one of Safety Harbor's most distinctive homes.

859 Harbor Hill Drive, Safety Harbor

$360,000

3 Beds ⋅ 3 Baths ⋅ TB8530268 MLS ⋅ 1750 BLDG.

CHARMING in CYPRESS TRACE NORTH ~ a BEAUTIFUL COMMUNITY in Safety Harbor. Cypress Trace North is known for its excellent location! LOCATION, LOCATION, LOCATION! FALL in LOVE with this BEAUTIFUL 3 bedrooms, 2 and a half bathrooms, and 1 carport townhome in Cypress Trace, one of the most sought after neighborhoods in Safety Harbor! YOU will LOVE this CUTEST 1,610 sq ft townhome! Pull up to LUSCIOUS landscape and BEAUTIFUL curb appeal. FALL in LOVE with the BEAUTIFUL exterior and be immediately drawn to the beauty of this home. As you enter through the FRONT DOOR of the home you will LOVE the abundance of natural light. YOU will be AMAZED by the SPACIOUS open floor plan, NEW refrigerator, 2 FIREPLACES, BONUS ENCLOSED FLORIDA ROOM, VAULTED ceilings, CROWN MOLDING, Water Softener, Water Heater (2021), AC (2013), Roof (2019), and much more. As you enter into the SPACIOUS COZY OPEN living room/dining combo room, you will LOVE its warmth and inviting atmosphere and LOVE entertaining in this room. The SPACIOUS OPEN kitchen overlooks a quaint breakfast nook sitting room. YOU WILL LOVE COOKING in the BEAUTIFUL EAT-IN kitchen with a BRAND NEW REFRIGERATOR (2026) and LARGE breakfast bar! This home is open and inviting ~ allowing the chef to be part of the activity! The indoor laundry closet is located in the kitchen, which offers much convenience. You will enjoy RELAXING with a book in the PEACEFUL ENCLOSED BONUS FLORIDA ROOM. YOU WILL ABSOLUTELY LOVE it and it's PERFECT for ENTERTAINING. This home offers a large primary bedroom suite upstairs with VAULTED CEILINGS, a FIREPLACE, a large walk-in closet, and en-suite bathroom with dual sinks, separate private water closet, and walk-in shower. Upstairs you will also find 2 more bedrooms and a full bathroom. This perfect family home has everything you could ever want! Come enjoy this quaint PEACEFUL townhome in ~ Cypress Trace North, which is one of the BEST locations close to DOWNTOWN Safety Harbor, Safety Harbor Spa, Philippe Park, beaches, airports, interstates, shopping, and restaurants! YOU will LOVE this MAINTENANCE FREE Community which offers a serene peaceful lifestyle, beautiful lake, tennis court, and pool. This townhome has NEVER FLOODED and is MOVE-IN READY! The HOA includes ~ CABLE TV and INTERNET, WATER, sewer, trash, roof repairs, lawn maintenance, community pool and spa, and much more! Enjoy this maintenance free lifestyle of living! YOU MUST SEE this little bit of Florida Paradise in this MAINTENANCE FREE COMMUNITY! **NOT IN A FLOOD ZONE.**

1750 Lake Cypress Drive Unit 1002, Safety Harbor

$1,399,900

4 Beds ⋅ 4 Baths ⋅ TB8526904 MLS

Virtually Staged. Welcome to one of Pinellas County’s most exceptional values in luxury new construction. Completed in 2025 and never occupied, this extraordinary waterfront pool home combines timeless architecture, impeccable craftsmanship, and designer finishes typically found in homes at a substantially higher price point. Situated on an oversized waterfront homesite, enjoy breathtaking sunsets, frequent dolphin sightings, abundant wildlife, and picturesque water views that define Florida luxury living. Offering 4 bedrooms, 4 full bathrooms, 3,433 square feet, and an oversized 3-car garage, this stunning residence showcases exceptional curb appeal with architectural millwork, stone accents, hurricane-impact windows, lush European-inspired landscaping, a spacious motor court, travertine walkways, and a welcoming covered front porch. Inside, soaring 10-foot ceilings and an open-concept floor plan create an inviting space for everyday living and entertaining. Engineered hardwood flooring, crown molding, custom wood ceiling beams, and a sleek electric fireplace complement walls of glass overlooking the pool and waterfront. The chef’s kitchen is a showpiece featuring ceiling-height custom cabinetry, premium quartzite countertops, under-cabinet and designer island lighting, a professional cooktop with designer hood, pot filler, built-in wall oven and microwave, and an oversized island overlooking the water. The first floor also includes a full guest bath and private en-suite bedroom, ideal for guests or multigenerational living. Upstairs, a custom wrought-iron staircase leads to a spacious loft and an incredible primary retreat featuring dual custom closets, a private waterfront balcony, and a spa-inspired bath with a freestanding soaking tub, oversized dual vanity, LED mirrors, smart toilet, and an oversized walk-in shower wrapped in imported floor-to-ceiling tile. Two additional bedrooms complete the second floor, including one with a private en-suite bath while the other shares a beautifully appointed hall bath. Both enjoy access to a second-story balcony. Outdoor living is equally impressive with an elevated resort-style pool, elegant cable railing, travertine decking with mosaic accents, tongue-and-groove wood ceilings, and expansive covered entertaining space overlooking the water. Additional upgrades include custom closet systems throughout, extensive millwork, whole-home water softener, reverse osmosis water filtration, epoxy garage flooring, premium lighting and fixtures, and countless designer touches throughout. Conveniently located near award-winning Gulf beaches, premier shopping, dining, top medical facilities, downtown St. Petersburg, Tampa, and Tampa International Airport, this remarkable residence delivers luxury, lifestyle, and exceptional value in one extraordinary package! Make your private appointment today.

3426 Channelside Court, Safety Harbor

$1,350,000

3 Beds ⋅ 2 Baths ⋅ TB8528153 MLS

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

$1,250,000

3 Beds ⋅ 3 Baths ⋅ TB8512600 MLS

One private acre in Safety Harbor. Rarely does a property like this become available. Nestled on a beautiful homesite in desirable Safety Harbor, this charming farmhouse-style residence, just minutes to downtown, offers the perfect blend of country living and modern convenience. The home features 3 generous bedrooms, 2.5 bathrooms, and two versatile bonus rooms that can be used as a home office, gym, playroom, guest space, or hobby room. Outside, enjoy your own backyard oasis with a sparkling Pebble Tec pool, expansive deck and grill area, covered outdoor living areas, and a detached air conditioned 3-car garage with breezeway to the house. The expansive acreage provides room for gardening, recreation, and endless possibilities. Enjoy the tranquility of country-style living. Walk, ride your bike or golf cart to beautiful Philippe Park featuring tree lined walkways, boat launch, picnic shelters and minutes from charming downtown Safety Harbor. Safety Harbor feels like a Hallmark movie come to life. Stroll to locally owned coffee shops, cozy wine bars, craft breweries, boutique shopping, the beloved Sunday Farmers Market, and year-round festivals that bring the community together. Spend an evening on the waterfront pier watching the dolphins and manatees surface in the bay, or enjoy the breathtaking sunsets along the shoreline. Privacy. Space. Flexibility. Opportunity. No HOA , High and Dry. This is Safety Harbor living at its finest. 4 Point inspection completed, Concrete Block , Roof 2007 no issues , 6 years remaining. 3 HVAC plus a mini split , 2021, 2025 and 2026,

3525 Fairview Street, Safety Harbor

$725,000

5 Beds ⋅ 3 Baths ⋅ O6420598 MLS

Virtually Staged. 37 Osprey St is a 2-story Safety Harbor single-family home built in 1983, laid out across five bedrooms and three bathrooms for everyday use. The kitchen centers on an island with a built-in sink that adds prep space and seating, paired with white cabinetry, dark stone countertops, a tile backsplash, stainless steel appliances, and recessed lighting for clear task visibility. A stone fireplace anchors the main living area beneath exposed wood ceiling beams, adding warmth and ambiance to the wood-look flooring. A bathroom provides double sinks to ease busy mornings, along with a separate soaking tub and a walk-in shower. A screened in-ground pool and fenced backyard extend the living space outdoors, and a 2-car attached garage completes this well-maintained residence with practical amenities throughout.. Included 100-Day Home Warranty with buyer activation

37 Osprey Street, Safety Harbor

$484,000

4 Beds ⋅ 3 Baths ⋅ TB8521049 MLS ⋅ 902 BLDG.

PRICE REDUCTION! Motivated Seller! Some townhomes feel like townhomes. This one doesn't. With over 2,000 square feet, a rare end-unit location, a 2-car garage, and a private backyard, this home offers the space, privacy, and feel of a single-family residence. Located in the highly desirable Village of Safety Harbor, you're just minutes from Main Street's award-winning restaurants, breweries, waterfront parks, festivals, and marina, while still enjoying a quiet neighborhood setting. Inside, the thoughtfully designed floor plan features multiple living spaces, updated finishes, abundant natural light, and exceptional storage throughout. The beautifully renovated kitchen offers quartz countertops, stainless steel appliances, an instant hot water dispenser, and even a refrigerator with a craft ball ice maker—perfect for entertaining. The first-floor primary suite provides everyday convenience, while upstairs you'll find three spacious bedrooms, including the only unit in the community featuring two private screened balconies. Step outside to your screened lanai overlooking a fully fenced backyard—large enough to accommodate a future pool, entertain guests, or simply enjoy the privacy that's nearly impossible to find in a townhome. Equally impressive is what you don't have to worry about. This home is not located in a flood zone, does not require flood insurance, and never flooded, even during the 2024 hurricanes when other homes within the HOA experienced water intrusion. Combined with one of the lowest HOA fees in the area, it offers peace of mind and exceptional value. Finding a 4-bedroom, 3-bath home with this much space, this many upgrades, a two-car garage, private yard, and this location in Safety Harbor for under $500,000 is incredibly rare. Whether you're looking for a primary residence, seasonal retreat, or simply more home for your money, this is an opportunity you won't want to miss. Schedule your private showing today and experience why this home stands in a class of its own! *Some photos are virtually staged*

902 Woodbridge Court, Safety Harbor

$600,000

4 Beds ⋅ 3 Baths ⋅ TB8522494 MLS

Virtually Staged. Welcome to this beautifully updated 4-bedroom, 2.5-bath home located in the highly desirable North Bay Hills community of Safety Harbor. Offering over 2,100 square feet of living space, this two-story residence combines modern updates, spacious living areas, and an unbeatable location in one of Pinellas County's most sought-after neighborhoods. A dramatic two-story foyer welcomes you inside, where soaring ceilings and abundant natural light create a bright and inviting atmosphere. The updated kitchen is designed for both functionality and style, featuring granite countertops, subway tile backsplash, stainless steel appliances, ample cabinetry, and generous prep space. The kitchen flows seamlessly into the main living and dining areas, creating an ideal layout for everyday living and entertaining. Upstairs, you'll find four spacious bedrooms, including a private primary suite complete with an updated ensuite bathroom and ample closet space. The additional bedrooms offer flexibility for family, guests, a home office, fitness room, or hobby space. Step outside to the screened lanai overlooking a large, fully fenced backyard with plenty of room for outdoor gatherings, pets, play equipment, or future backyard enhancements. Whether enjoying your morning coffee or hosting weekend barbecues, this outdoor space offers endless possibilities. Major updates provide peace of mind, including a newer roof and updated HVAC system. Additional features include a convenient half bath on the main level, indoor laundry, and a two-car garage. Ideally situated just minutes from charming downtown Safety Harbor, residents enjoy easy access to local shops, restaurants, parks, the Safety Harbor Marina, Philippe Park, top-rated schools, Tampa International Airport, and the world-famous Gulf beaches. With its combination of space, updates, and prime location, this home presents an exceptional opportunity to enjoy the Florida lifestyle you've been searching for.

4163 Mallard Drive, Safety Harbor

$1,350,000

TB8517758 MLS

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

$940,000

6 Beds ⋅ 5 Baths ⋅ TB8512678 MLS

Exceptional Location next to Phillippe Park's Main Entrance in Safety Harbor for this Remodeled 2 story Home. A total of 5,843 sq-ft & 3,802 sq-ft Heated Sq-Ft. 5 Beds, 4 Baths in the Main House and a 480 sq-ft 1 bed/1 bath Guest house over a 640 Sq Ft Garage. The Whole on a 120 x 117 Ft lot. Feature: A large bean shaped pool, screened in with stone Deck & oversized Porch. New kitchen with new appliances, Double glass windows, Hurricane Shutters. French doors, new colonial shatters on every window. New fixtures, LED bulbs & electronic mirrors. Many closet spaces. New carpet, Travertine Floor. 3-year-old Roofs. New gutters. Smart A/C thermostat & Smart water heater control Wi-Fi. Osmosis system for the entire Property. Storm Drainage outside & a Sump Pump stabilizer inside. Too much to list … Ready to move-in Amazing Property, located on a serene, charming street, near Downtown Safety Harbor & all Amenities.

2436 Navarez Avenue, Safety Harbor

$1,849,900

4 Beds ⋅ 4 Baths ⋅ TB8515695 MLS

Pre-Construction. To be built. Experience the perfect blend of luxury, coastal charm, and modern design in this stunning new construction home located in the heart of downtown Safety Harbor. Thoughtfully designed for both everyday living and entertaining, this exceptional residence offers 4 bedrooms, 3 bathrooms, a dedicated study, spacious loft, and a private garage apartment. Step inside to discover an open-concept floor plan centered around a designer kitchen featuring a large island, abundant cabinetry, and seamless flow into the dining and living areas. Expansive glass doors open to the covered lanai, creating the ultimate indoor-outdoor lifestyle.The first-floor owner's retreat offers a peaceful escape with a spacious walk-in closet and luxurious spa-inspired bath complete with dual vanities, soaking tub, and oversized shower. Upstairs, a generous loft creates an additional gathering area ideal for a media room, playroom, or second living space. Two secondary bedrooms and a full bath provide comfortable accommodations for family and guests. Adding incredible versatility, the property also includes a private garage apartment featuring its own living room, kitchen, bedroom, and full bath - ideal for guests, multigenerational living, a home office, or income-producing opportunities. Enjoy outdoor living from the covered lanai, with ample backyard space and the option to add a custom pool. Just a short walk from Safety Harbor's charming Main Street, Safety Harbor Spa, restaurants, shops, and year-round community events, this home offers the rare opportunity to enjoy new construction in one of Tampa Bay's most desirable downtown communities. The unique three-car garage configuration provides exceptional storage for vehicles, golf carts, and recreational equipment.

215 2nd Avenue N, Safety Harbor

Safety Harbor Homes with Two Story Style

Newest Safety Harbor Homes with Two Story Style

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