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 quaint, small-town atmosphere, South Pasadena offers a delightful blend of picturesque landscapes and vibrant community life. With its close proximity to the stunning Gulf of Mexico, residents enjoy easy access to pristine beaches, lush parks, and a wealth of recreational activities that make everyday living feel like a vacation.

One of the most enchanting features of South Pasadena is its unique architectural landscape, particularly the charming homes designed in the Cottage style. These homes exude warmth and character, often featuring inviting front porches, steeply pitched roofs, and whimsical details that evoke a sense of nostalgia. The Cottage architectural style is perfect for those seeking a cozy retreat, whether you’re a first-time homebuyer or looking to downsize.

In South Pasadena, you'll find a variety of Cottage-style homes that seamlessly blend modern amenities with classic charm. Many of these residences boast beautifully landscaped yards, perfect for enjoying Florida's sunny weather or hosting friendly gatherings. The community is also known for its friendly neighbors and low-key vibe, making it an ideal place for families, retirees, and everyone in between.

With its rich history, strong sense of community, and beautiful homes, South Pasadena is not just a place to live; it’s a place to thrive. Come explore the delightful streets and discover the perfect Cottage home that could be your next sanctuary in this beautiful corner of Florida!

Newest South Pasadena Homes with Cottage Architectural style

$159,000
2 Beds ⋅ 2 Baths ⋅ Town Shores Of Gulfport SubDv. ⋅ 33707 Zip Code
A first-floor corner home in Gulfport's Town Shores with a covered carport spot (furnishings negotiable)—a welcoming 55+ waterfront community on Boca Ciega Bay—does not come along every day- this one. This bright 2-bedroom, 2-bath Jamison House residence offers 1,170 square feet, windows on three sides, mature landscaping and true ground-floor living. The lifestyle begins right outside your door with one of the community's four heated pools—The Jamison's pool was just renovated and is HEATED year round, directly off your back patio - plus tennis, pickleball, bocce, shuffleboard, fitness room, saunas, billiards, library, ballroom, marina and kayak launch. Historic Gulfport’s beach, Williams Pier, restaurants, colorful shops and live entertainment are only a few blocks away. The seller reports that this unit did not experience interior flooding during the 2024 hurricanes. Inside, white Shaker-style cabinetry, warm butcher-block countertops and stainless steel appliances give the updated kitchen a crisp coastal feel. The split-bedroom layout adds privacy, while the spacious primary suite offers an updated private bath and walk-in closet. A garden-view Florida room works beautifully as an office, reading room or morning-coffee retreat, and tile flooring keeps upkeep simple. Less upkeep, more Gulfport—and a first-floor corner unit worth seeing. All information to be verified with the HOA. Boat slips are available on a 1st come 1st serve basis.

2960 59th Street S Unit 101, Gulfport
$475,000
4 Beds ⋅ 2 Baths ⋅ Pasadena Heights SubDv. ⋅ 33707 Zip Code
Seller agrees to offer $10k to buyer for closing costs or rate buy down at closing! 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
$995,990
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
$375,000
2 Beds ⋅ 1 Baths ⋅ Boca Ceiga Park SubDv. ⋅ 33707 Zip Code
This charming retreat is located in the vibrant downtown area of Gulfport just a few blocks from Beach Boulevard where you’ll discover eclectic shops, art galleries, lively restaurants/bars plus the popular Tuesday Fresh Market. Enjoy unbeatable proximity to the Gulfport Pier, marina, beach, parks, playgrounds, recreation center, theatre & library. With year-round events & activities plus quick access to downtown St. Petersburg & the Gulf beaches, this location truly offers the best of Florida living. Step inside this elevated, vintage 2 bedroom, 1 bath home & be greeted by a spacious enclosed front porch perfect for morning coffee or evening wine. The bright living room features hardwood floors flowing into a dining area & galley kitchen. Both bedrooms fit queen size beds with the larger bedroom offering a walk-in closet for added convenience. There is a detached studio with a bathroom & laundry room. The fully fenced yard backs up to an alley & includes a storage shed along with ample off-street parking via a long brick driveway. Newer roofs, A/C and main water heater. Recent termite treatment with a transferable warranty. Located in the AE flood zone. Fantastic investment opportunity, vacation home or winter escape. Furnishings & décor are negotiable. Don’t miss your chance to own this unique, vintage Gulfport gem.

2907 Clinton Street S, Gulfport
$185,000
3 Beds ⋅ 2 Baths ⋅ Causeway Village 55 An Dup SubDv. ⋅ 33707 Zip Code
Beautifully maintained and move-in ready 3-bedroom, 2-bath mobile home located in a desirable South Pasadena waterfront community. Built in 2016 (Nobility) and offering 1,344 sq ft, this home has been meticulously cared for and thoughtfully upgraded. Major improvements include a brand-new roof (2025) with full replacement, City permits, 130-mph rated shingles, wind mitigation, and warranty, along with new A/C and new ductwork, updated flooring, and a remodeled guest bathroom. The home also features a permitted aluminum carport, pavered entry, storage shed, and numerous exterior enhancements. The open floor plan offers spacious living and dining areas, a well-appointed kitchen with a new over-the-range microwave (2024), and generous bedroom sizes. Monthly pest control service has been professionally maintained since purchase. HOA fee is $895/month and includes lot rent and property taxes, as well as access to all community amenities. Community Amenities Include: Heated swimming pool Waterfront access with dock Clubhouse Shuffleboard courts Conveniently located near beaches, shopping, and dining, this turn-key mobile home offers the perfect blend of comfort, affordability, and resort-style Florida living. Buyer to verify room dimensions and sf are approximate

1375 Pasadena Avenue S Unit 217, South Pasadena
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