South Pasadena Homes with Sidewalk Exterior Features

South Pasadena Homes with Sidewalk Exterior Features

Welcome to South Pasadena, Florida – a hidden gem nestled in the heart of Pinellas County! This charming city boasts a unique blend of small-town charm and modern conveniences, making it the perfect place to call home. With its picturesque tree-lined streets, vibrant community, and a welcoming atmosphere, South Pasadena offers a lifestyle that is both relaxed and engaging.

One of the standout features of homes in this delightful city is the emphasis on outdoor living, particularly those with sidewalk exterior features. Imagine taking leisurely strolls along the meticulously maintained sidewalks, where neighbors greet each other with warm smiles and friendly waves. These homes are designed to foster community connections, encouraging residents to enjoy the beautiful Florida weather and engage with one another.

South Pasadena is conveniently located just a stone’s throw away from the stunning Gulf Coast beaches, offering endless opportunities for sun-soaked days and breathtaking sunsets. The city is also home to a variety of parks, shops, and dining options, ensuring that everything you need is within easy reach. Whether you’re exploring the local boutiques or savoring a meal at one of the charming eateries, you’ll find that South Pasadena has something for everyone.

With its inviting atmosphere, beautiful homes featuring sidewalk exteriors, and proximity to the best of Pinellas County, South Pasadena is not just a place to live – it’s a place to thrive. Come discover the charm and warmth of this wonderful city, where your dream home awaits!

Newest South Pasadena Homes with Sidewalk Exterior Features

$195,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Bring your personal style and discover the possibilities in this 2-bedroom, 2-bath condo in the Avalon Building at Town Shores of Gulfport. With a solid foundation and plenty of potential, just a few thoughtful updates could transform this home into a fresh, inviting Florida retreat tailored to your taste. Some of the work is already done. The shared bath has been refreshed with newer tile, a walk-in shower, and an updated vanity, and French doors open from the primary bedroom into an enclosed Florida room, a bright bonus space ready to become a home office, reading nook, hobby room, or guest retreat. An assigned carport space keeps your car covered and close to home. Located in a beautifully maintained 55+ waterfront community along Boca Ciega Bay, the Avalon Building offers a friendly atmosphere and convenient access to everything that makes Town Shores such a desirable place to call home. Whether you're looking for a full-time residence or a sunny Florida getaway, this condo presents an opportunity to update at your own pace while enjoying the community and lifestyle from day one. Town Shores is known for its impressive collection of resort-style amenities, including four heated swimming pools, tennis and pickleball courts, a fitness center, shuffleboard, billiards, a library, marina, and scenic waterfront walking paths. Spend your mornings strolling along Boca Ciega Bay, your afternoons by the pool, and your evenings enjoying everything nearby Gulfport has to offer. Just minutes away is Gulfport's colorful waterfront district, filled with locally owned restaurants, boutiques, art galleries, entertainment, and popular markets and community events. Browse the Tuesday Fresh Market on the bay, catch a dance or concert at the historic Gulfport Casino Ballroom, or paddle the mangroves at Clam Bayou Nature Preserve. Stetson University College of Law is right around the corner, the Gulf beaches of St. Pete Beach are about 10 minutes away, and downtown St. Petersburg is roughly 20 minutes by car, making this Gulfport FL condo an easy home base for 55+ living in Pinellas County.

5840 30th Avenue S Unit 201, Gulfport
$345,000
2 Beds ⋅ 2 Baths ⋅ Chateau Tower Condo SubDv. ⋅ 33707 Zip Code
Welcome to Paradise Living at Chateau Towers!  This beautifully renovated, second-floor condo offers 2 spacious bedrooms and 2 bathrooms and boasts beautiful waterfront views of Boca Ciega Bay. This unit comes completely furnished and is turn key ready.  Relax on your private balcony, watching beautiful sunset skies over the Gulf of Mexico.  Step inside to find an open floor plan, perfect for entertaining.  The kitchen features new white shaker cabinets with quartz counters, and stainless steel appliances.  All new easy care luxury vinyl plank flooring and 5 inch baseboards.  The laundry closet is conveniently located next to the kitchen.  The primary ensuite is tucked at the back of the condo featuring a tranquil water view, along with a large walk-in closet and renovated bath.  The second bedroom and bathroom are at the front of the unit, for added privacy.  The water heater is brand new, and the AC is only 3-4 years old.  Resort-style amenities include a waterfront heated pool, hot tub, and a fitness center.  The community also features a sauna, steam room, outdoor grills, a bike rack, a party room with a kitchen, a library, and a recreation room with a billiard table, ping pong table, and shuffleboard.  Store your kayak on the property and launch it into the Bay, where you can paddle alongside dolphins and manatees.  Prime Pasadena location...just 5 minutes from the award-winning St Pete Beach and Treasure Island, with easy access to Publix, Walmart, a variety of dining options, and a quick 20-minute drive to exciting downtown St Pete.  This is coastal living at its finest!

7050 Sunset Drive S Unit 211, South Pasadena
$1,300,000
3 Beds ⋅ 3 Baths ⋅ Boca Ceiga Park SubDv. ⋅ 33707 Zip Code
Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 3 bedrooms, 3 bathrooms, and 3,051 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door. Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income. Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring, and a whole-house reverse osmosis system deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy. Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked. Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5417 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.

5417 Essex Avenue S, Gulfport
$1,499,000
10 Beds ⋅ 7 Baths ⋅ Veteran Park SubDv. ⋅ 33707 Zip Code
Three side-by-side properties, one rare Gulfport opportunity. 5025, 5027 & 5029 28th Ave S are sold together: 7 rental units in 4 classic 1949 buildings on over half an acre, blocks from Beach Blvd, the waterfront and Casino Ballroom. Four 2BR/1BA units, two 1BR/1BA units and a detached studio cottage, with covered porches, garden path, green space and off-street parking. Currently rented and producing income. Flood Zone X, no HOA/CDD. Package sale only. Owner is a licensed FL broker.

5025 28th Avenue S, Gulfport
$449,000
4 Beds ⋅ 2 Baths ⋅ East Pasadena SubDv. ⋅ 33707 Zip Code
Opportunities like this are hard to find in St. Pete. This 4 bedroom, 1.5 bath home sits on a large 100' x 127' corner lot and gives the next owner a lot more than just a house. The home has just over 1,500 sq ft of living space, a 2022 roof, detached 390 sq ft garage, alley access, and some of the original character that makes these St. Pete homes stand out. Inside you’ll find wood beams, arched details, cove ceilings, a skylight, and a wood-burning fireplace. The real value here is in the land and what you can do with it. Yes - updates and a beautiful pool would be amazing. But the new build potential is where even more value is if you have development on your mind. The property can be split into two separate lots, with the ability to build a home and an ADU on each lot. That opens up a lot of possibilities depending on what you want to do. Keep the existing home and enjoy the extra land, renovate it and make it your own, build new, or take advantage of the development potential and create multiple living spaces on one property. The corner lot and alley access make the layout even more useful, whether you are thinking about future construction, additional parking, a new garage, or separate access for an ADU. You are also just minutes from the beaches, Downtown St. Pete, restaurants, shopping, and everything that makes this part of St. Pete so desirable. A 4 bedroom home on a large corner lot is already hard to find. Add a newer roof, detached garage, alley access, two buildable lots, and the ability to build a home and ADU on each one, and you have a property with a lot of upside.

6190 2nd Avenue S, St Petersburg
$195,000
2 Beds ⋅ 2 Baths ⋅ Shore Towers Bldg SubDv. ⋅ 33707 Zip Code
Welcome to waterfront living at Shore Towers, a 55+ community where sweeping views of Boca Ciega Bay set the stage for the Florida lifestyle! This fourth-floor, two-bedroom, two-bathroom condo offers 1,075 square feet of comfortable living space with an open, inviting layout and wood-look flooring throughout. The updated kitchen features granite countertops, abundant cabinetry, stainless-steel appliances, a desirable gas range and an expansive breakfast bar that opens to the main living area, ideal for casual dining and entertaining. Just beyond the living room, the spacious Florida room is surrounded by windows showcasing beautiful views of the bay and manicured waterfront grounds. Use this versatile space for dining, relaxing, a home office or simply watching the boats pass by. Hurricane windows and remote-controlled hurricane shutters provide additional protection and peace of mind. Both bedrooms offer generous space and ample closet storage, while two full bathrooms add everyday convenience. Additional storage is included for all your beach gear and everyday essentials. Shore Towers offers an impressive waterfront setting with a resort-style pool, private fishing dock, shuffleboard, community laundry room and elevator. Residents also enjoy a secure-entry clubhouse with exercise equipment and seasonal social events, including holiday parties. Launch your kayak directly from the property, then return for an afternoon by the pool or an evening cookout at the waterfront patio featuring BBQ grills and outdoor dining. Kayak storage is included, and the owners are leaving a kayak for the new owner to enjoy. This is your opportunity to experience relaxed waterfront living on beautiful Boca Ciega Bay!

1868 Shore Drive S Unit 409, South Pasadena
$450,000
5 Beds ⋅ 2 Baths ⋅ Pasadena Gardens Gulfview Sec SubDv. ⋅ 33707 Zip Code
Welcome to this charming and unique income-producing property situated on a HUGE oversized lot of nearly 1/4 acre, just minutes from the vibrant heart of Downtown Gulfport! Offering an incredible combination of character, versatility, outdoor space, and investment potential, this property presents an exciting opportunity for both investors and owner-occupants alike. The property features a quaint 3-bedroom, 1-bath main cottage, along with a separate 2-bedroom, 1-bath apartment located above the spacious 2-car garage. Adding even more convenience and appeal for investors, the two residences are separately metered for BOTH WATER AND ELECTRIC, allowing for easier management of utilities and added flexibility for rental arrangements. The property also features a ROOF FROM 2018, and AC units from 2021 and 2025, providing another valuable improvement for future owners. This flexible setup offers multiple possibilities—live in the main home while generating additional income from the apartment, create a comfortable space for extended family or guests, or take advantage of both residences as an income-producing investment. Outside is where this property truly shines. The expansive, fully fenced backyard offers an incredible amount of space rarely found this close to Downtown Gulfport. A large covered patio creates the perfect setting for outdoor dining, entertaining, weekend gatherings, or simply relaxing and enjoying the Florida lifestyle. And for an extra touch of fun, the backyard even features your very own private PUTTING GREEN! For investors and buyers with a vision, the property offers tremendous value-add potential. With some thoughtful cosmetic updates and improvements, there is an excellent opportunity to enhance both the appeal and overall value of the property while maximizing its income-producing potential. Enjoy the charm and laid-back lifestyle Gulfport is known for, with Downtown Gulfport's eclectic restaurants, local shops, art galleries, entertainment, waterfront district, and community events just minutes away. Whether you're searching for your next investment, looking to offset your mortgage with rental income, or dreaming of a property with room for multiple generations, this versatile property offers endless possibilities.

5401 21st Avenue S, Gulfport
$399,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Breathtaking Boca Ciega Bay views and beautiful sunsets take center stage in this oversized condo located in the highly sought-after 55+ community of Town Shores of Gulfport. From the moment you enter, your eyes are drawn to the expansive water views from the generous living and dining area, creating a beautiful backdrop for everyday living and entertaining. The primary suite features a walk-in closet, tons of natural light, and a private ensuite bath, while the spacious guest bedroom also offers a walk-in closet with a full guest bath conveniently located just outside the bedroom. The kitchen provides plenty of cabinet space and pantry. This condo has been thoughtfully updated with luxury vinyl flooring, a newly replaced bay window, and new HVAC in 2026. Additional conveniences include a private storage area and designated parking space. Town Shores is known for its impressive resort-style amenities, including four swimming pools, a marina with boat slips available for rent subject to availability, tennis, pickleball, bocce ball, shuffleboard, a fitness room, his-and-her saunas, and an expansive clubhouse featuring a large billiards room, multiple meeting spaces, and generous common areas. Best of all, you are just minutes from vibrant downtown Gulfport, where you can enjoy locally owned restaurants, shops, art, community events, and Gulfport Beach. Whether you are relaxing at home watching the sun set over Boca Ciega Bay or taking advantage of everything this active waterfront community has to offer, this is Florida living at its best.

6020 Shore Boulevard S Unit 211, Gulfport
$220,000
2 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to beautifully updated living in Town Shores, a sought-after 55+ community in the charming town of Gulfport! This move-in-ready 2/1 condo has been thoughtfully refreshed throughout, offering a fresh, modern feel from the moment you walk in. The completely remodeled kitchen features new appliances and updated finishes, creating a stylish and functional space for everyday living and entertaining. Brand-new luxury vinyl plank (LVP) flooring flows throughout the condo, complemented by new baseboards and fresh interior paint for a clean, cohesive look. Located in the desirable Town Shores community, residents enjoy a relaxed Florida lifestyle with an array of amenities and activities. Just minutes from the waterfront, Gulfport's vibrant downtown, restaurants, shops, and beaches, this condo offers the perfect combination of comfort, convenience, and community. Whether you're looking for a full-time residence, seasonal getaway, or a place to enjoy the best of Florida living, this beautifully updated condo is ready to welcome you home!

3010 59th Street S Unit 306, Gulfport
$150,000
1 Beds ⋅ 1 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
FULLY FURNISHED... And, completely UPDATED, this beautiful, like-new, condo has been renovated top to bottom! This spacious 1060 square foot interior features continuous luxury vinyl plank (LVP) flooring throughout, creating a stylish seamless look. Enjoy peace of mind with a walk-in shower, a beautifully updated kitchen featuring all new stainless-steel appliances. Move right in and enjoy the comfort and convenience of a truly turnkey home. The deeded carport is just steps and two guest spots right in front of your front door! Enjoy worry-free living with cable TV, internet, gas (for cooking and heating), and more... included in your monthly HOA fee... you only pay for electricity! Residents of Town Shores enjoy an impressive array of amenities including a fitness center (gym), billiards, room with a dozen pool tables, indoor shuffleboard tables, a library and multiple game rooms. Outdoor recreation options include shuffleboard, bocce ball, tennis and pickleball courts. The community also offers four heated pools (two right on Boca Ciega Bay) and a vibrant social clubhouse! Located just three blocks from the charming waterfront district of Gulfport, residents can easily enjoy a variety of local restaurants, boutiques, art galleries and entertainment. And don't forget the very active Senior Center located just a few blocks away, with many activities to enjoy daily! Convenient public transportation provides easy access to St. Petersburg, the nearby beaches and destinations throughout Pinellas County. Not to mention, only 10 minutes from award winning Gulf beaches, and 30 minutes to St Petersburg and Tampa International Airports. Call today to see this beauty in person! It won't last long at this price!

3018 59th Street S Unit 111, Gulfport
$998,500
2 Beds ⋅ 2 Baths ⋅ Kipps Colony At Pasadena Yacht/Cntry Club SubDv. ⋅ 33707 Zip Code
TOP-FLOOR WATERFRONT LIVING AT KIPPS COLONY IN PASADENA YACHT & COUNTRY CLUB! Beautifully updated, this spacious residence with a loft combines soaring vaulted ceilings, waterfront views and exceptional boating amenities in one of the area's most desirable gated communities. Recent improvements include wide-plank luxury vinyl flooring throughout, an updated kitchen with white cabinetry, quartz countertops, new stainless steel appliances, as well as beautifully updated baths. Walls of sliding glass doors fill the open great room with natural light and lead to a spacious waterfront balcony. Electronic blinds in the living room and electronic hurricane shutters provide effortless privacy, light control and storm protection at the touch of a button. The expansive primary suite features soaring vaulted ceilings and a walk-in closet, while the extensively updated primary bath offers abundant custom cabinetry and storage. The second bedroom offers en-suite bath access and features a custom Murphy bed/desk system, negotiable with the sale. A standout feature is the upper-level loft, ideal for a home office, den or flex space, with water view and a new mini-split A/C and a new pneumatic elevator providing convenient access from the main living level. FOR BOATERS, THIS ONE IS EXCEPTIONAL: the residence includes a LARGE DEEDED DEEP-WATER BOAT SLIP (approx. 53' x 17') WITH A 19,000-LB BOAT LIFT—an increasingly coveted amenity for Tampa Bay boating—along with TWO COVERED PARKING SPACES and a private storage cage. Kipps Colony 1 residents enjoy a waterfront pool and spa and a pet-friendly lifestyle within gated Pasadena Yacht & Country Club, conveniently located near Gulfport, St. Petersburg and the Gulf beaches. Eligible buyers also have the opportunity to bypass the PYCC full golf membership waitlist and apply for club membership within the first 30 days of ownership. Milestone and reserve studies have been completed, and any assessments have been paid. Conveniently located just minutes from Florida's famous beaches, a short drive to Downtown St Petersburg and a brief 35-40 minute to Tampa!

2775 Kipps Colony Drive S Unit 305, Gulfport
$259,000
2 Beds ⋅ 2 Baths ⋅ Golfview I Condo SubDv. ⋅ 33707 Zip Code
Contemporary style, a functional open floor plan, and an exceptional location come together in this tastefully updated 2-bedroom, 2-bath condo in Golfview I Condominiums. Situated directly across from Stetson University College of Law, you'll be minutes from Gulfport's lively waterfront district, eclectic Beach Boulevard, award-winning Gulf beaches, downtown St. Petersburg, and countless destinations for dining, shopping, entertainment, and recreation. Designed for easy living, the floor plan flows naturally from the spacious living room into the dining area and kitchen, creating comfortable spaces for everyday life and effortless entertaining. Gleaming wood floors bring warmth to the living room, while tile flooring throughout the remainder of the home offers durability, low maintenance, and a cohesive look. Neutral finishes provide the perfect backdrop for virtually any decorating style. The kitchen combines clean design with everyday practicality, featuring granite countertops, stainless steel appliances, and a dedicated glass washer at the sink—a thoughtful upgrade that's rarely found. Just beyond, the adjoining dining area offers an ideal setting for everything from a quick breakfast before work to leisurely dinners with family and friends. The primary suite includes a private bathroom, while the second bedroom features an oversized double closet and convenient access to the hall bath. A separate laundry room with washer and dryer keeps household tasks neatly tucked away. The A/C was replaced six years ago, and the water heater was installed in 2016. Bordering the Pasadena Yacht & Country Club golf course, Golfview I offers residents beautifully landscaped grounds, a saltwater swimming pool, gazebo and lounge areas, perfect for unwinding after a day at work or on the golf course. Two furnished guest suites are available for rent by family and friends of residents, subject to availability and advance reservations, making extended visits easy and comfortable. The community welcomes up to two pets, cats or dogs, with a maximum weight of 50 pounds/dog. Owners may lease their unit with a minimum rental period of only three months, providing excellent flexibility for seasonal residents, investors, or anyone seeking additional options for future use. Living in Gulfport means becoming part of one of Tampa Bay's most distinctive communities. Known for its vibrant arts scene, independently owned restaurants, galleries, boutiques, live music, festivals, weekly markets, historic Casino Ballroom, marina, and year-round community events, Gulfport offers a character all its own. Spend the afternoon exploring Beach Boulevard, enjoy dinner overlooking Boca Ciega Bay, browse the monthly Art Walk, paddle through nearby waters, or gather with friends to watch another unforgettable Florida sunset. There is always something to experience. Whether you're searching for a primary residence, a winter escape, or an investment opportunity, this move-in-ready condo offers an outstanding opportunity to enjoy the Gulfport lifestyle while staying close to everything that makes the greater St Petersburg area one of Florida's most desirable places to live.

6100 Gulfport Boulevard S Unit 405, Gulfport
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