Pinellas County Homes with Cottage Architectural style

Pinellas County Homes with Cottage Architectural style

Welcome to Pinellas County, Florida, a coastal gem that offers a delightful blend of sun-soaked beaches, vibrant communities, and a rich cultural tapestry. Nestled along the Gulf of Mexico, this stunning county is renowned for its picturesque waterfronts, lush parks, and a plethora of recreational activities. Whether you’re a nature enthusiast, beach lover, or someone who enjoys the arts, Pinellas County has something for everyone.

One of the most charming architectural styles gracing this region is the cottage style home. These quaint, cozy residences exude warmth and character, making them a beloved choice for many homebuyers. Typically characterized by their inviting front porches, steeply pitched roofs, and delightful gardens, cottage homes create a sense of nostalgia and comfort. In Pinellas County, you’ll find these charming abodes nestled in serene neighborhoods, often just a stone's throw from the stunning beaches and vibrant local attractions.

Living in a cottage home in Pinellas means embracing a lifestyle that celebrates community and the great outdoors. Enjoy morning strolls along tree-lined streets, afternoons spent at nearby parks, and evenings watching the sunset over the Gulf. With the added benefit of a welcoming community spirit, residents often find themselves engaged in local events and activities.

Whether you’re looking to buy your first home or seeking a vacation retreat, Pinellas County’s cottage-style homes offer a unique opportunity to experience the beauty of Florida living. Discover the charm of cottage life in this enchanting coastal paradise today!

Newest Pinellas County Homes with Cottage Architectural style

1672 Rainbow Drive, Clearwater
$318,916
2 Beds ⋅ 1 Baths ⋅ Keystone Manor Rev SubDv. ⋅ 33755 Zip Code
Adorable 1955 Clearwater cottage with charm, updates, and plenty of outdoor space! This well-maintained block home features a 2021 roof and major 2022 updates including the kitchen, bathroom, electrical, hot water heater, appliances, and fresh paint. Additional improvements include a privacy fence and irrigation system (2023), attic insulation (2025), water softener and refrigerator (2026), plus more! Luxury wood-look vinyl flooring flows throughout, with tile in the kitchen and bathroom. The kitchen opens to the dining and family areas, keeping everyone connected. Two spacious bedrooms provide comfortable living space. Step outside to the open patio overlooking the private backyard—perfect for entertaining, gardening, or play. Only a 15 minutes drive to the sandy beaches of Clearwater Beach! Walk to Crest Lake Park and A-rated Skycrest Elementary School. Don’t miss this Clearwater gem!

1672 Rainbow Drive, Clearwater
1206 Bay Shore Boulevard, Indian Rocks Beach
$615,000
2 Beds ⋅ 1 Baths ⋅ Indian Beach Re-Revised 1st Add SubDv. ⋅ 33785 Zip Code
A refreshed Indian Rocks Beach retreat offering a great combination of location, low-maintenance living and flexibility. Located on a 51 x 109 lot along Bay Shore Boulevard, this inviting home is just across the street from the Intracoastal Waterway, ONE block from 15th Ave Resident Boat Ramp and TWO blocks from Kolb Park, putting boating, recreation and the best of the beach-town lifestyle right outside your door. Inside, the home has been comprehensively updated (permits included!). Buyers will enjoy gleaming, durable terrazzo flooring throughout the living spaces, abundant natural light and a fresh, comfortable interior with new kitchen appliances. Major improvements also include a 2022 roof and 2025 HVAC (elevated above any flood impacts). Outside, the fully pavered backyard creates an easy, low-maintenance space for relaxing, entertaining or enjoying the Florida sunshine. A one-car garage with epoxy flooring and a storage shed with ramp access add valuable flexibility for storage, hobbies, beach gear and more. For those looking for more than a primary residence, the location also offers interesting investment possibilities as a Short- or Long-term rental -- subject to applicable regulations & fees per the City of Indian Rocks Beach. The home may also be purchased furnished (negotiable) making it an especially convenient option for buyers looking to settle in & begin enjoying their Indian Rocks Beach lifestyle immediately. Whether you're looking for a low-maintenance place to call home, a coastal getaway or an investment opportunity, this well-positioned Bay Shore Boulevard property is worth a closer look!

1206 Bay Shore Boulevard, Indian Rocks Beach
821 Paris Avenue S, St Petersburg
$200,000
2 Beds ⋅ 1 Baths ⋅ District Fla Corp Sub 1 SubDv. ⋅ 33701 Zip Code
Property being sold totally AS-IS. Fixer Upper opportunity! This property is ready for your vision & offers an exciting chance for investors, renovators, and savvy buyers. Bring your plans and transform this property into a profitable flip, rental or long term investment. There's a concrete parking pad in the backyard, which has a new wood privacy fence.

821 Paris Avenue S, St Petersburg
629 Lexington Street, Dunedin
$374,000
2 Beds ⋅ 1 Baths ⋅ Doroma Park 1st Add SubDv. ⋅ 34698 Zip Code
LIVE THE DUNEDIN DREAM! Just off the bustling streets of historic Downtown Dunedin sits this charming 2-bedroom, 1-bath bungalow with a versatile bonus room, offering the perfect combination of character, updates, and an unbeatable location. From the moment you arrive, you’ll love the inviting front porch—the perfect spot to enjoy your morning coffee before heading downtown. Step inside to a bright, welcoming interior featuring luxury vinyl plank flooring, 5-inch baseboards, newer double-pane windows, and plenty of natural light. The open kitchen features newer shaker cabinets and overlooks the oversized, fully fenced backyard with a shed and plenty of room to add a pool. Major improvements provide added peace of mind, including ALL NEW PLUMBING IN 2025, a NEW TANKLESS WATER HEATER, upgraded electrical panel and new electrical outlets, a 2019 ROOF, and a 2016 A/C. The laundry room includes a washer and dryer that convey with the property. The flexible Florida room/bonus room offers additional space for a home office, guest room, or additional living area. Covered parking provides room for both your vehicle and golf cart, while the carport offers potential to be converted into a garage or additional living space. The spacious side yard also provides room to store your BOAT OR RV. Best of all, this move-in-ready home is NOT IN A FLOOD ZONE and puts you just moments from everything that makes Downtown Dunedin so special. Hop on your golf cart and enjoy the restaurants, TD Ballpark, breweries, shops, festivals, waterfront, and vibrant downtown lifestyle. Don’t miss your opportunity to own your own piece of the Dunedin Dream. SEE YOU DOWNTOWN!

629 Lexington Street, Dunedin
2706 Gulf Boulevard, Indian Rocks Beach
$1,995,000
2 Beds ⋅ 3 Baths ⋅ Indian Beach Re-Revised SubDv. ⋅ 33785 Zip Code
Offered at $2,195,000, 2706 Gulf Blvd is a completely reimagined, turnkey coastal residence just steps from the Gulf of America in the heart of Indian Rocks Beach. Positioned on the desirable west side of Gulf Boulevard and offered fully furnished, this exceptional property combines the feel and finish of a newly completed home with Commercial Tourist (CT) zoning and short-term vacation-rental potential. Virtually every component has been replaced, upgraded or thoughtfully redesigned. Major improvements include a new roof, 200-amp electrical service, new plumbing and PVC sewer lines, front and rear backflow improvements, natural gas, gas heat, tankless hot water heater, new HVAC systems including a mini-split in the Florida room, and approximately 100 additional square feet of conditioned living space. All exterior windows and doors are high-impact hurricane rated. Special attention was also given to coastal resilience. All entry points are equipped with custom FlowStop aluminum flood barriers, providing an additional layer of protection against potential water intrusion. Combined with impact-rated windows and doors, updated underground plumbing and backflow improvements, the home has been thoughtfully upgraded for coastal living. Inside, everything has been transformed with new tile flooring, interior doors, closets, lighting, finishes and fixtures. The kitchen features new cabinetry, stone countertops and Kitchen Aid, stainless steal appliances. All three bathrooms are completely new, including a shower added to the former half bath. An interior wet bar, new washer and dryer, alarm and security camera systems complete the turnkey interior. Outside, a new heated in-ground pool anchors a private resort-style setting surrounded by new pavers, artificial turf, fencing, landscaping, trees and plantings. Additional improvements include a sprinkler system, storage shed, hot-and-cold outdoor shower, exterior lighting and fully pavered driveway. The property is offered FULLY FURNISHED with new furniture, TVs, Bose soundbars, linens, towels, smallwares and household essentials—ideal for a buyer seeking a turnkey beach residence or furnished investment property. Adding to its appeal is CT zoning and the absence of HOA or condominium leasing restrictions, providing flexibility for primary residence, second-home or short-term vacation-rental use, subject to applicable City of Indian Rocks Beach registration, licensing and operating requirements. Just steps from the beach, the property offers the walk-to-the-Gulf lifestyle sought by vacationers and second-home buyers alike. Whether enjoyed as a luxury residence, Florida beach retreat or furnished income-producing vacation property, 2706 Gulf Blvd delivers a rare combination of beach proximity, extensive new improvements, private heated pool, hurricane protection, dedicated flood-mitigation features, flexible zoning and turnkey furnished delivery in one of Pinellas County's most desirable Gulf Coast communities.

2706 Gulf Boulevard, Indian Rocks Beach
2363 4th Avenue N, St Petersburg
$779,000
4 Beds ⋅ 3 Baths ⋅ St Petersburg Investment Co Sub SubDv. ⋅ 33713 Zip Code
Welcome to this historic Craftsman bungalow radiating authentic charm, character, and versatility in Historic Kenwood. This unique compound features a standalone 2-bedroom, 2-bathroom main house alongside a detached garage and a fully independent Accessory Dwelling Unit (ADU). The spacious ADU offers a complete 2-bedroom, 1-bathroom floor plan with its own full living room, kitchen, dedicated address, and electric meter—delivering incredible potential for rental income, multi-generational living, or a private home office setup. Real hardwood floors run throughout both the main house and the ADU, perfectly complementing the home's historic architectural details. Out back, enjoy a private, low-maintenance outdoor oasis featuring a fully turfed backyard completely enclosed with a low-maintenance vinyl fence. Situated on a desirable corner lot, another highlight is the expansive driveway leading to the detached garage, providing rare and abundant off-street parking for multiple vehicles. Major high-ticket system updates: All three structures feature durable metal roofs installed in 2021, all water lines were updated with PVC in 2023, and the ADU boasts a newer A/C system. Enjoy the unbeatable Historic Kenwood lifestyle—just minutes from the Grand Central District, downtown St. Pete, local parks, and top dining. Call me to schedule your private showing today!

2363 4th Avenue N, St Petersburg
129 94th Avenue, Treasure Island
$625,000
2 Beds ⋅ 1 Baths ⋅ Harrells Addie B Sub SubDv. ⋅ 33706 Zip Code
Welcome to Paradise, Sunset Beach is Living the Dream.This Beautiful Home is a short distance to the Gulf and the White Sandy Beach. Sunsets 365 Days a year and enjoy the only Restaurant on Sunset Beach Caddy’s Waterfront Restaurant with Great Food and Spirits. KaTiki’s is a must visit for the Music Lovers and there is NO COVER and Music of a Variety of Genre’s of Live Music and Offers a Wide Variety of Spirits for your enjoyment listening or Dancing to Live Music until 11:00 PM. Now for your New Home. Enter into the large Living Room with Cathedral Ceilings ; New Flooring and Hurricane Proof Windows. Two new Split Window Units so quiet you can’t hear them cooling your Home. Solid Wood Doors, not Hollow Doors; a walk in Closet and another Closet in the Bedroom. Custom Built with Solid Wood Doors. House has been rewired by a Licensed Contractor with new Outlets and a newly Rewired Electrical Box. With Fans in the Living Room, Kitchen and Master Bedroom and a Washing Machine and Dryer in the garage easily reached off the Back Deck in the Garage. Family Restaurants within a short distance or take your Golf Cart and each Restaurant has a different theme from American Cuisine to Italian cuisine or Authentic Mexican cuisine. The Publix Grocery store is 1.1 miles from the Home and there is a Walgreens 1.3 miles away. This House is the best Destination for Living Beach Life surrounded by Amenities we want for Year Round Living or spending Winter in the Sunshine State.

129 94th Avenue, Treasure Island
6100 35th Avenue N, St Petersburg
$379,900
2 Beds ⋅ 2 Baths ⋅ Sheryl Manor Unit 1 Pt Rep SubDv. ⋅ 33710 Zip Code
Rare privacy this close to downtown St. Petersburg! Tucked away on a quiet cul-de-sac street, this light-filled 2-bedroom, 2-bath home sits on more than a quarter acre and offers an exceptional sense of seclusion. The beautiful primary suite features a private en-suite bathroom and abundant natural light. Bedroom 2 includes an attached private bonus room—ideal for a home office, sitting room, or potential conversion into a third bedroom. Gorgeous white terrazzo flooring flows throughout much of the home, complemented by luxury vinyl flooring in the rear flex space. Recessed lighting, fresh interior and exterior paint, new kitchen cabinetry, energy-efficient impact windows, a high-quality water-filtration system, and a durable metal roof provide comfort, efficiency, and lasting value. Outside, the expansive yard offers ample room to explore adding living space, a large pool, or an incredible outdoor-entertaining area. Towering pine trees create a beautiful natural backdrop with no immediate rear neighbor, while the home’s placement on the oversized lot provides additional privacy from neighboring homes on both sides. Relax on the charming front porch and enjoy a peaceful setting—all just minutes from vibrant downtown St. Petersburg. A truly special property offering space, flexibility, privacy, and possibilities rarely found this close to the city!

6100 35th Avenue N, St Petersburg
2329 15th Avenue S, St Petersburg
$225,000
2 Beds ⋅ 1 Baths ⋅ Delmonte Sub SubDv. ⋅ 33712 Zip Code
A nice sized 2 bedroom 1 bath home with nice sized lot and a 3-4 car concrete driveway. This home is located near the Tropicana Field, the Interstate and Downtown with all of its restaurant and music. A bus stop is nearby making commuting convenient. House should qualify for down payment assistance.

2329 15th Avenue S, St Petersburg
1419 55th Street S, Gulfport
$459,000
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
1945 Overbrook Avenue, Clearwater
$419,000
2 Beds ⋅ 2 Baths ⋅ Sunset Point 2nd Add SubDv. ⋅ 33755 Zip Code
NEW PRICE! Welcome to your slice of Florida sunshine! Tucked on a beautiful street just minutes from Downtown Dunedin's restaurants, breweries, shops, and festivals, this completely renovated, move-in-ready cottage is bursting with charm. Inside, you'll find 2 bedrooms, 2 full baths, PLUS a dedicated office that flexes beautifully into a third bedroom. Step inside and fall in love with the bright, open floor plan and fresh, stylish finishes — every inch has been done for you, so just bring your boxes! Out back? A large backyard with room to dream big: add a pool, plant a garden, or create the ultimate sunset-watching retreat. And what a location! Just moments from the water, where jaw-dropping sunsets and sparkling water views are simply part of your evening routine. Hop on the nearby Pinellas Trail for a morning ride or sunset stroll, and you're a quick ride to Downtown Dunedin! Better yet — high and dry with NO flood zone! Renovated, flexible, and moments from the water, the trail, and downtown — homes like this don't come around often!

1945 Overbrook Avenue, Clearwater
3530 51st Avenue N, St Petersburg
$274,900
2 Beds ⋅ 1 Baths ⋅ Lellman Heights 1st Sec SubDv. ⋅ 33714 Zip Code
Welcome home to this charming cottage that has been fully restored and styled to honor its historic origins! You'll find that the new quartz countertops, matte black finishes and freshly installed luxury laminate flooring add subtle modern convenience to make this quaint home completely move-in ready. Once you're settled in, pour up a glass of your favorite beverage and enjoy your large back yard from within the fully screened-in back lanai. Have peace of mind knowing this house is sturdy sitting on a concrete perimeter footer and situated on one of the higher points in St Pete, NON FLOOD ZONE. The large yard is fully fenced in, with a double gate allowing for secure and discreet RV or boat storage. All major components have been updated recently: Roof was permitted in 2020 (with an extra degree of protection w/ peel and stick underlayment), AC, electric panel and water heater also updated around 2020. Schedule a tour today to start your next chapter!

3530 51st Avenue N, St Petersburg
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