South Pasadena Homes with Sidewalk Exterior Features

South Pasadena Homes with Sidewalk Exterior Features

Welcome to South Pasadena, Florida – a charming coastal gem nestled in the heart of Pinellas County. Known for its picturesque streets and vibrant community spirit, South Pasadena offers a unique blend of small-town charm and modern conveniences. Just a stone's throw away from the beautiful Gulf of Mexico, this delightful city boasts stunning beaches, lush parks, and a plethora of recreational opportunities that beckon both residents and visitors alike.

One of the standout features of South Pasadena is its commitment to walkability. The city is adorned with homes that showcase inviting sidewalk exterior features, encouraging leisurely strolls through the neighborhood. Imagine stepping outside your front door and being greeted by tree-lined streets, friendly neighbors, and the soothing sounds of nature. Whether you're taking a morning jog or enjoying an evening walk with loved ones, the sidewalks create a sense of community and connection that is truly special.

The real estate market in South Pasadena is diverse, offering a variety of homes that cater to different lifestyles and preferences. From charming bungalows to modern townhouses, there’s something for everyone. Many properties feature beautifully landscaped yards and outdoor spaces perfect for entertaining or simply enjoying the Florida sunshine.

With its prime location, friendly atmosphere, and beautiful homes with sidewalk exterior features, South Pasadena is not just a place to live; it’s a place to thrive. Come discover the warmth and charm of this delightful city, where every day feels like a vacation!

Newest South Pasadena Homes with Sidewalk Exterior Features

$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
$357,700
2 Beds ⋅ 1 Baths ⋅ Pasadena Gardens Gulfview Sec SubDv. ⋅ 33707 Zip Code
There is something undeniably appealing about a classic Gulfport bungalow, and this beautifully updated 2-bedroom, 1-bath home gets the balance just right. Original character and charm remain, including a wonderful original fireplace that anchors the living space, while the important updates have already been thoughtfully completed. The result is a home that feels authentic, comfortable, and completely move-in ready. Inside, natural light complements the home's warm bungalow character, with the original fireplace serving as a reminder of the history and personality that make homes like this so special. The fully renovated kitchen features quartz countertops and a Whirlpool stainless steel appliance suite, while the updated bath feels fresh and polished. Behind the scenes, many of the improvements buyers appreciate most have already been addressed, including a newer roof, new impact glass windows, updated electrical wiring and plumbing, and a new tankless water heater. Just off the kitchen, a quiet screened lanai creates the perfect spot for morning coffee, an evening cocktail, or simply enjoying Gulfport's laid-back Florida lifestyle. The oversized corner lot may be one of this property's best surprises. There is plenty of room for boat, RV, or trailer parking, with additional space to consider a future pool, home addition, or expanded outdoor living area. A separate freestanding structure adds even more possibilities. Use it as a home office, art studio, workshop, she-shed, creative space, or explore converting it back to its original use as a carriage house garage. For buyers looking beyond a primary residence, the home's turn-key condition and Gulfport location also create excellent potential as an income-producing property. Best of all, the property sits high and dry in desirable FEMA Flood Zone X, an increasingly important consideration for Florida buyers. Updated where it matters, rich with the original character that gives a Gulfport bungalow its personality, and offering considerably more flexibility than its charming footprint might suggest, this is a home that makes it very easy to imagine calling Gulfport home.

1601 54th Street S, Gulfport
$244,900
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
Welcome to the amazing waterfront community of Town Shores of Gulfport. This completely renovated 2-bedroom, 2-bath condo located on the second floor is waiting for you. The kitchen was beautifully renovated in 2022, windows were replaced in 2023, and new flooring was completed in 2024.The primary bedroom offers a spacious walk-in closet with a custom closet system for exceptional storage and organization and a bathroom renovated in 2024. The community has several pools, Tennis courts and many fun activities. You will spend your evenings watching the spectacular sunset. Enjoy easy Florida living in a beautifully updated home close to Gulfport’s charming waterfront, shops, restaurants, and beaches. Just a short drive to downtown St. Pete and Tampa. Don't miss out on the opportunity to own this wonderful updated condo today.

5840 30th Avenue S Unit 202, Gulfport
$364,900
3 Beds ⋅ 2 Baths ⋅ SubDv. ⋅ 33707 Zip Code
BEAUTIFULLY RENOVATED | 3 BEDROOMS | 2 BATHROOMS | 1,104 SQ FT | NO HOA Behind the welcoming front porch of this classic St. Petersburg bungalow is a bright, design-forward interior that feels completely fresh while preserving the character that makes the home special. THE BIG UPDATES ARE ALREADY DONE: NEW KITCHEN, NEW STAINLESS STEEL APPLIANCES WITH WARRANTIES, TWO NEWLY FINISHED BATHROOMS, NEW WIDE-PLANK FLOORING, NEW WATER HEATER, NEW LIGHTING AND FIXTURES, AND A ROOF REPLACED IN 2016. Natural light fills the living room, where decorative wall molding and the fireplace create a warm and memorable focal point. The new wide-plank flooring carries throughout the home, tying together the crisp white finishes, warm wood tones, matte-black hardware, and carefully selected lighting. The kitchen is the true showpiece. White shaker cabinetry, sleek countertops, a full-height backsplash, an oversized island, pendant lighting, and a complete suite of new stainless steel appliances create a space that looks just as impressive in person as it does in the photos. The private primary suite brings a boutique-hotel feel with a warm wood double vanity, dual mirrors, matte-black fixtures, a glass-enclosed walk-in shower, and a custom walk-in closet. The second bathroom continues the same elevated design with a modern wood vanity, stylish fixtures, and a tub. Outside, the fully fenced corner lot provides double-gate access, a generous parking pad, and plenty of usable outdoor space. The covered front porch adds even more charm and gives the home a welcoming first impression. Conveniently located near Gulfport, St. Pete Beach, downtown St. Petersburg, shopping, dining, and major roadways. This is not a basic cosmetic update—it is a stylish, thoughtfully finished home where character, design, and everyday function come together beautifully.

5355 2nd Avenue S, St Petersburg
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