South Pasadena Homes with Cottage Architectural style

South Pasadena Homes with Cottage Architectural style

Welcome to South Pasadena, Florida, a charming coastal city nestled in the heart of Pinellas County. Known for its warm, inviting atmosphere and picturesque surroundings, South Pasadena offers a delightful blend of suburban tranquility and vibrant urban life. Just a stone's throw from the beautiful Gulf of Mexico, residents enjoy easy access to pristine beaches, stunning sunsets, and an array of recreational activities. With its proximity to bustling St. Petersburg and the vibrant arts scene, South Pasadena is an ideal location for those seeking a relaxed lifestyle without sacrificing convenience.

One of the standout features of South Pasadena is its unique architectural charm, particularly the enchanting homes designed in the Cottage style. These delightful residences exude character and warmth, often characterized by their quaint, inviting facades, steeply pitched roofs, and charming details. Many of these cottages are surrounded by lush gardens and mature trees, creating a serene environment that feels like a retreat from the hustle and bustle of everyday life.

Living in a Cottage-style home in South Pasadena means embracing a lifestyle that values comfort and community. These homes often feature cozy interiors with thoughtful layouts, perfect for both entertaining and relaxation. Imagine sipping your morning coffee on a sun-drenched porch or hosting friends in a charming living room adorned with vintage accents.

In South Pasadena, you’ll find a welcoming community that cherishes its history and the beauty of its surroundings. Whether you’re a first-time homebuyer or looking to downsize, the Cottage-style homes in this delightful city offer a unique opportunity to experience Florida living at its finest. Come discover the charm of South Pasadena today!

Newest South Pasadena Homes with Cottage Architectural style

5313 19th Avenue S, Gulfport
$415,500
2 Beds ⋅ 1 Baths ⋅ Pasadena Gardens Gulfview Sec SubDv. ⋅ 33707 Zip Code
Discover the charm of Gulfport living in this inviting bungalow, offering a wonderful blend of vintage character, thoughtful modern updates, and the relaxed coastal vibe that makes Gulfport so special. The home features attractive porcelain tile flooring, new carpeting in primary bedroom, and new laminate flooring in the bonus room (October 2026). The kitchen is a knockout, showcasing custom design details, Restoration Hardware-inspired lighting, custom concrete countertops, subway tile backsplash, under-cabinet lighting, a farmhouse-style porcelain sink, over-the-range vent hood, and built-in wine rack. The bathroom has also been tastefully updated. A versatile bonus room offers additional living/flex space or potential 3rd bedroom. The oversized garage provides ample room for laundry, a vehicle, and workshop space, while the extra-deep adjacent carport offers additional covered parking. Numerous important improvements include a new fence installed in 2025, plumbing redone in 2022, windows and doors replaced in 2020/2021, HVAC system replaced in 2020, and roof replaced in 2019. Step outside and enjoy the tropical landscaping, lush lawn that has been certified as a natural habitat, a covered deck, and an adjacent patio area perfect for relaxing, entertaining, or enjoying Florida's year-round outdoor lifestyle. The privacy fenced yard provides plenty of room for gardening, pets, and outdoor enjoyment. Full of character, flexible living space, and meaningful updates, this Gulfport bungalow offers a wonderful opportunity to enjoy the unique charm and laid-back lifestyle of one of Pinellas County's most beloved waterfront communities!

5313 19th Avenue S, Gulfport
1419 55th Street S, Gulfport
$415,000
4 Beds ⋅ 2 Baths ⋅ Pasadena Heights SubDv. ⋅ 33707 Zip Code
Over $100,000 in upgrades—including a brand-new 400 sq ft addition with two new bedrooms and a luxurious master bathroom—have transformed this charming Gulfport home into a modern retreat. Enjoy the best of both worlds: perfectly situated along the vibrant Pinellas Trail for biking, jogging, and leisurely walks, yet tucked away on a remarkably quiet corner lot that offers serenity and privacy. Located just 5 minutes from world-famous St. Pete Beach, this move-in ready home sits in a no-flood zone and features a brand-new roof (2025), new gutters, fresh exterior paint, new fencing, new electrical upgrades, and a tent treatment for termites completed in 2025—offering true peace of mind and low-maintenance living for years to come. Step outside your door and experience the best of Gulfport’s thriving coastal lifestyle. From the legendary weekly farmers market and 500-foot fishing pier to boutique shopping, local art galleries, and waterfront dining, you’re just minutes from everything this dynamic community has to offer. Don’t miss your chance to own this beautifully remodeled, corner-lot home in a rapidly appreciating neighborhood—schedule your private showing today and make this exceptional property yours!

1419 55th Street S, Gulfport
5631 23rd Avenue S, Gulfport
$970,990
3 Beds ⋅ 3 Baths ⋅ Lake Butler Villa Cos Add SubDv. ⋅ 33707 Zip Code
Pre-Construction. To be built. WinWay Homes offers a 3 Bed, 2 Bath, 1 Half Bath, 2 Car Garage, 2166 sf custom home located in Gulfport in the beautiful historical district. The spacious open floor plan features a stunning granite island overlooking the open family and dinning looking out 12' sliding glass doors. Relax with a beverage on a large covered lanai with enough room to add an optional pool and outdoor kitchen in the backyard. The master suite with spacious walk-in closet and double french glass doors leading to 372sf covered lanai. The master bath with a spa-inspired floor to ceiling walk-in wet area, with optional multiple shower heads, and free-standing tub offers the ultimate tranquil experience. Standard features will include shaker cabinetry, tile backsplash, granite vanity in all bathrooms, energy efficient water heater, LED lighting, in wall pest control, USB outlets, ventilated shelving, 2-10 home warranty, land tile flooring. Additional options will be offered including, gourmet kitchen, privacy fence, pool and spa, and the list continues. Exterior features include optional brick paver drive and sidewalk, James Hardie shake siding, and custom-tailored landscaping. Contract now to choose your options, colors, and styles. Additional Floorplans Available.

5631 23rd Avenue S, Gulfport
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