Pinellas County Homes with Key West Architectural style

Pinellas County Homes with Key West Architectural style

Welcome to Pinellas County, Florida—a vibrant coastal gem that perfectly blends sun-soaked beaches, lush parks, and a thriving community spirit. Nestled on the Gulf of Mexico, Pinellas boasts a delightful array of activities and attractions, from the stunning shores of Clearwater Beach to the charming shops and restaurants of Dunedin. This picturesque county is not only known for its natural beauty but also for its rich cultural offerings, including art galleries, music festivals, and a variety of outdoor recreational opportunities.

One of the most enchanting architectural styles you’ll find in Pinellas County is the Key West style, a delightful homage to the laid-back elegance of the Florida Keys. Homes adorned with Key West architecture often feature vibrant pastel colors, inviting front porches, and metal roofs that reflect the sunshine. These residences are designed to embrace the coastal lifestyle, with open floor plans that invite the gentle ocean breeze and ample windows that frame breathtaking views.

Imagine sipping your morning coffee on a breezy porch, surrounded by swaying palm trees and the soothing sounds of waves lapping at the shore. Key West-style homes in Pinellas are not just residences; they are a lifestyle choice, offering a unique blend of comfort and charm. With spacious layouts, tropical landscaping, and proximity to pristine beaches, these homes are a true sanctuary for those seeking a slice of paradise.

Whether you’re looking to buy your first home or seeking a vacation retreat, Pinellas County’s Key West architectural gems offer a perfect blend of style, comfort, and coastal living. Discover your dream home today in this enchanting corner of Florida!

Newest Pinellas County Homes with Key West Architectural style

2665 Beagle Path Way, Palm Harbor
$1,225,000
5 Beds ⋅ 5 Baths ⋅ Country Woods SubDv. ⋅ 34683 Zip Code
Discover this exceptional, highly maintained, custom quality constructed distinctive Victorian-style Luxury residence w/ amazing curb appeal, covered brick front porch, located in coveted Country Woods Subdivision, where timeless architecture throughout meets exceptional amenities for Florida living! This truly special Palm Harbor/Dunedin Area residence offers 5 bedrooms, 5 baths including outdoor Cabana bath, 2.5 Car Garage, common area gathering rooms/spaces throughout for daily living/entertainment flexibility for the entire family, guests, with multigenerational living possibilities. Upon entry you are greeted by a spacious open concept floor plan, vaulted ceilings, waterproof luxury vinyl wood flooring in the main part of the house. A separate elegant Formal Dining room is perfect for special occasions featuring spectacular double high Rotunda Ceiling w/ windows, wood flooring, service built-ins. Formal Living Room w/ sliding glass doors leads to a huge, covered lanai with classic pavers, tremendous amounts of storage cabinetry, granite countertop spaces, outdoor kitchen, sink, appliances, custom banquet table storage, lounging area w/ gas fire pit, heated Saltwater Pool/Spa w/ Cabana Bathroom/shower. At the heart of the home an updated Chef’s kitchen of style/function features Cherry Wood Cabinetry by K&M Custom Cabinetry, classic granite countertops, farm style copper sink, curated appliances, massive island with large storage cabinets, pull out drawers, double beverage fridge, complete with countertop seating/casual dining space. The adjoining Family Room features a brick/gas fireplace, a convenient digital media/study/workspace, LG CineBeam UHD 4K projector w/ a drop down cinema screen/surround-sound audio for an immersive home-theater experience. A wood spiral staircase leads to a dedicated 2nd floor game room, wood flooring, private bath, wet bar and audio speaker system. The 1st floor Primary Bedroom Suite features an expansive layout of separate spaces including large private bedroom w/ gas fireplace, huge walk-in closet with built in shelving, a private bathroom suite w/ high design double vanity sinks, granite countertops, custom cabinetry, 2-person double head rain showers, custom free-standing bathtub. The 1st floor also has a convenient spacious 2nd bedroom w/ custom built-in wood bookcase, and a full-size laundry rm w/ access to a covered outdoor lanai. An extra-wide, custom-built wood staircase leads to 2nd floor Jack-and-Jill 3rd and 4th bedrooms with an adjoining updated bathroom, the Game Room, and large 5th bedroom (currently used as fitness room). The backyard areas feature a large water fountain, frog pond, 3,300-gallon Koi and Duck Pond Oasis w/ cascading waterfalls, wood bridge, tropical landscaping, slate walkways, all viewable from an elevated screened side yard porch. NEW 2025 shingle/metal roof, 3 Trane AC systems: 2026, 2020, 2012. FEMA Flood Zone X. Enjoy nearby downtowns of Palm Harbor/Dunedin, local shops, restaurants, breweries, entertainment venues. Explore Honeymoon Island State Park, Gulf Coast scenery, World Class beaches, walking/biking trails. Golf enthusiasts can enjoy Dunedin Golf Club/PGA Innisbrook Resort. Nearby Tampa International Airport, St. Pete/Clearwater Airport, and multiple sporting venues. With its Victorian character, resort-inspired outdoor amenities, this one-of-a-kind property offers the opportunity to call home, and enjoy the Florida lifestyle. A must see!

2665 Beagle Path Way, Palm Harbor

19417 Gulf Boulevard Unit D206, Indian Shores
$340,000
1 Beds ⋅ 1 Baths ⋅ Barefoot Beach Resort Of Indian Shores SubDv. ⋅ 33785 Zip Code
TURNKEY BEACH RETREAT & INVESTMENT OPPORTUNITY! Enjoy coastal living at Barefoot Beach Resort in beautiful Indian Shores! This fully furnished upstairs 1-bedroom, 1-bath condo features an open floor plan, a versatile bonus room with potential to accommodate up to six guests, and a convenient laundry room just outside the front door. Coastal-inspired décor, tile flooring, crown molding, abundant storage, and a fully equipped kitchen with granite countertops make this residence move-in ready. This waterfront resort spans five acres along approximately 400 feet of Intracoastal Waterway and offers a heated pool, sun deck, fishing dock, BBQ grills, outdoor dining, and potential access to private boat slips. Enjoy private deeded beach access just across the street! A compelling opportunity for investors seeking a flexible beachside rental property or a second home with income potential. With no minimum rental period restrictions, owners can choose on-site management, an independent rental company, or self-management, while retaining the flexibility to enjoy the property personally. Future bookings transfer with the sale and must be honored by the new owner. Conveniently located near restaurants, shopping, John's Pass, downtown St. Petersburg, and the Suncoast Beach Trolley. The seller reports no damage from the 2024 hurricanes. Seize the opportunity to own a turnkey property in a sought-after Gulf Coast destination. Make your move toward beachside ownership and potential rental income—schedule your showing today!

19417 Gulf Boulevard Unit D206, Indian Shores

1430 Gulf Boulevard Unit 407, Clearwater Beach
$749,000
2 Beds ⋅ 2 Baths ⋅ Sand Key Condo-South Beach 2 SubDv. ⋅ 33767 Zip Code
Trade the to-do list for endless sunshine at South Beach on Sand Key ~ the ultimate destination for effortless Florida beachfront living! This beautifully updated condo offers breathtaking views of both the Gulf and the Intracoastal Waterway, giving you the rare opportunity to enjoy stunning sunrises and unforgettable sunsets every single day. Step inside to a bright and open floor plan designed to maximize the sparkling blue water views from nearly every room. The beautifully appointed kitchen features granite countertops, tile backsplash, stainless steel appliances and an extended breakfast bar with seating for casual dining and entertaining. The spacious family room flows seamlessly to the oversized private balcony, where jaw-dropping panoramic views of the Gulf, Intracoastal waters and powdery white sandy coastline create the ultimate backdrop for relaxing or hosting guests. The spacious primary suite offers direct balcony access, dual closets and a spacious primary bath. The guest bedroom also features balcony access and beautiful water views, making every space in this home feel connected to the beauty of Sand Key. This condo has been thoughtfully updated with fresh interior paint, luxury vinyl plank flooring and professional luxury fabric blinds throughout (2026). Additional upgrades include a new hurricane-rated family room window, kitchen refrigerator and UV light for the AC (2025), new HVAC system, ceiling fans and replaced rollers on the patio hurricane shutters (2024), a new PGT slider door in the primary suite and high efficiency stacked washer and dryer (2023), plus a new water heater and updated closet doors (2022). Best of all, this incredible condo comes completely furnished so you can immediately start living your best beach life! South Beach on Sand Key is one of the Gulf Coast’s most desirable beachfront communities, offering direct access to award winning white sandy beaches just minutes from all the dining, entertainment and excitement of Clearwater Beach. This structurally sound building has passed all three condo inspections and maintains fully funded reserves, allowing you to invest with confidence. Residents enjoy resort style amenities including a heated waterfront pool, poolside and beachside tiki huts, fitness center, elegant club room and 24 hour gated security. HOA fees include internet, cable, water, sewer, trash, exterior maintenance, building insurance, and outstanding community amenities. Experience the peaceful, upscale coastal lifestyle that makes Sand Key one of Florida’s true Gulf Coast gems!

1430 Gulf Boulevard Unit 407, Clearwater Beach

2511 Dolly Bay Drive Unit 104, Palm Harbor
$291,700
2 Beds ⋅ 2 Baths ⋅ Dolly Bay A Village On Lake Tarpon SubDv. ⋅ 34684 Zip Code
MOVE-IN READY | UPDATED | 1,611 SQ. FT. | LAKE TARPON WATERFRONT COMMUNITY! Welcome to Dolly Bay, one of Palm Harbor’s hidden waterfront gems! This spacious 2-bedroom, 2-bath condo offers 1,611 sq. ft. PLUS an enclosed lanai overlooking a serene tropical nature setting. Thoughtfully remodeled and well maintained, this home is move-in ready and offered furnished (optional) for the seller’s convenience. Inside, enjoy a spacious layout with NO CARPET, abundant storage, a large galley kitchen with NEW refrigerator, WET BAR, indoor laundry and pantry/storage area. The enclosed lanai features DOUBLE-PANE INTERIOR SLIDERS and HURRICANE-RATED WINDOWS throughout—creating a peaceful space to enjoy the beautiful nature views. The oversized primary suite features TWO WALK-IN CLOSETS, an ensuite bath with a large ROUND JACUZZI TUB and separate linen closet. The generously sized second bedroom, full hall bath and foyer closet provide even more space and storage. Major improvements include NEW HVAC, NEW HOT WATER HEATER, NEW REFRIGERATOR, NEW METAL ROOF (2024), popcorn ceilings removed, hurricane-rated lanai windows, double-pane interior sliders and numerous additional updates. With just 84 residences, Dolly Bay offers a charming, neighborly atmosphere surrounded by mature trees, tranquil ponds, scenic boardwalks and Florida wildlife—all with DIRECT ACCESS TO LAKE TARPON, one of Pinellas County’s premier freshwater lakes for boating, fishing, kayaking and paddleboarding. Community amenities include a HEATED LAKEFRONT POOL, clubhouse, tennis courts, waterfront boardwalk, fishing dock, fish-cleaning station, community fire pit, picnic area with BBQ grills and private Lake Tarpon access. BOAT SLIPS are available first-come, first-served (currently $1,000/year), with KAYAK STORAGE currently available for $100/year. One assigned parking space plus ample guest parking. Conveniently located near John Chesnut Sr. Park, Pinellas Trail, Gulf beaches, shopping, dining, golf, healthcare and both St. Pete-Clearwater and Tampa International Airports. Imagine boating across Lake Tarpon for lunch or dinner at Tarpon Turtle, fishing at sunrise, kayaking peaceful waters or relaxing around the community fire pit. Ideal as a PRIMARY RESIDENCE, SEASONAL RETREAT or INVESTMENT OPPORTUNITY. It’s more than a home—it’s the Florida waterfront lifestyle. WELCOME TO DOLLY BAY!

2511 Dolly Bay Drive Unit 104, Palm Harbor

19201 Vista Lane Unit D2, Indian Shores
$625,000
3 Beds ⋅ 3 Baths ⋅ Vista Village Twnhms SubDv. ⋅ 33785 Zip Code
Vista Village Townhomes – With views of the sparkling Intracoastal Waterway, and about a block from the white sugar sands of Indian Shores Beach, this elevated 3 Bedroom Townhome has 3 full baths and a 3-car tandem garage. The open kitchen has white shaker cabinets with matte black hardware, stainless appliances, double sink and white subway tile backsplash. The breakfast bar provides a casual serving space with a flexible and more traditional dining area. The living room has sliding doors to a private balcony overlooking the waterfront and community pool. The main living level also includes the third bedroom and a full bath. The upper level provides stunning water views from the Primary Suite and private balcony. The Primary Ensuite Bath has double vanity and walk-in shower with new glass shower doors. The Second Suite, also with a private bath, has a cozy window seat enjoying tropical treetop views. The laundry on this level includes newer full-sized washer and dryer. A beach parking “dream-come-true”, you will love being able to park in your own THREE CAR garage. Even the garage has a private patio! The location, just off 193rd Avenue, is across the way from the public beach access, nestled right between Indian Shores Coffee Shop and Salt Rock Grill. From Sunrise to Sunset - you can plan your entire day around coffee, beach and cocktails! The low monthly HOA fee of $365 includes water, trash and reserves for roof. Vista Village is a pet friendly community, welcoming residents of all ages. With a 30-day minimum rental period, this Townhome presents flexibility as a quiet full-time residence or a lucrative investment opportunity. This fully furnished townhome has newer HVAC and Appliances. It is move-in ready and even includes a kayak to help kickoff your new Florida Lifestyle!

19201 Vista Lane Unit D2, Indian Shores

5050 Coquina Key Drive Se, St Petersburg
$430,000
2 Beds ⋅ 2 Baths ⋅ Waterside At Coquina Key South SubDv. ⋅ 33705 Zip Code
IMAGINE WAKING UP, OPENING THE BLINDS, AND TAKING IN EXPANSIVE, UNOBSTRUCTED VIEWS OF TAMPA BAY. Welcome to 5050 Coquina Key Dr SE, a beautifully updated two-level waterfront townhome where the water becomes part of your everyday surroundings. Inside, hurricane-rated windows frame the views, while the updated kitchen features custom cabinetry, granite countertops, stainless steel appliances, a wine refrigerator, and a spacious island. Step outside onto the large paver patio surrounded by lush landscaping and enjoy the waterfront setting just steps from your door. Launch a kayak or paddleboard, relax by the nearby community pool, or simply enjoy the views of Tampa Bay. Whether used as a primary or seasonal residence, this property offers the opportunity to enjoy Florida waterfront living while remaining just minutes from Downtown St. Petersburg. At the current listing price, SELLER IS OFFERING TO PAY THE RECENTLY APPROVED $25,730.64 SPECIAL ASSESSMENT AT CLOSING, subject to the terms of an accepted contract. If financed through the association's stated payment schedule rather than paid in full, the assessment is approximately $714.74 per month for 36 months, in addition to the regular HOA assessment. Buyers and buyers' agents should independently verify the assessment amount, payment schedule, HOA fees, and all association information directly with the association and applicable documents. The gated waterfront community offers 24-hour guarded access, a community pool, fitness center, yacht club and clubhouse facilities, tennis, pickleball and basketball courts, shuffleboard, playground, walking areas, boat-slip opportunities, and access to Tampa Bay for boating, kayaking, and paddleboarding. This isn't just about living near the water. It's about waking up to it

5050 Coquina Key Drive Se, St Petersburg

10495 Longwood Drive, Largo
$419,900
2 Beds ⋅ 2 Baths ⋅ Arbors At Bardmoor The SubDv. ⋅ 33777 Zip Code
INVESTORS, RENOVATORS & VALUE-SEEKERS, THIS IS THE OPPORTUNITY YOU'VE BEEN WAITING FOR! Offered at just $419,900, this Seminole property is priced to create immediate attention and offers tremendous upside for the buyer with vision. Bring your contractor, your imagination and your calculator! This is your chance to purchase a home in an established neighborhood where nearby properties are currently being offered at substantially higher prices, including an updated home next door offered at $659,900 and another nearby property offered at $599,000. This home is being sold as a FIXER-UPPER / HANDYMAN SPECIAL and is priced accordingly. No pretending it's something it isn't. It needs updating and improvement, but that's exactly where the opportunity lies. Renovate it, modernize it and potentially unlock significant value. Whether you're an investor looking for your next project, a contractor searching for an opportunity, or an owner-occupant willing to put in some sweat equity, 10495 Longwood Drive deserves your immediate attention. At $419,900, the seller has priced this property with one objective: GET IT SOLD. Properties with this kind of price differential don't come along every day. Seller's loss can be your gain. Bring your best offer, your renovation ideas and your vision, because at this price, we expect buyers to take notice quickly. CASH, RENOVATION LOAN & CONVENTIONAL BUYERS, COME TAKE A LOOK. Opportunity is knocking at 10495 Longwood Drive.

10495 Longwood Drive, Largo

103 Royal Court, Safety Harbor
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Philippe Pointe SubDv. ⋅ 34695 Zip Code
Nestled on a premier corner cul-de-sac lot within Safety Harbor’s highly coveted Philippe Pointe neighborhood, the elevated Key West-style retreat at 103 Royal Ct stands as a masterclass in sophisticated coastal living. Expertly manicured grounds frame this grand estate, where a permanent natural buffer ensures absolute privacy, and panoramic views of Old Tampa Bay stretch across the horizon. Every morning here begins with a brilliant sunrise dancing across the water, while evenings showcase the distant, glistening lights of the Tampa skyline. The journey inside begins through custom leaded glass front doors that open up to a grand, sun-drenched main level where formal and casual spaces flow seamlessly together. For ultimate convenience and accessibility, a private home elevator (professionally installed in 2020 and updated with a brand-new backup battery in 2026) effortlessly connects the home's levels. To the left of the foyer, an expansive dining room sets an elegant stage for hosting, while straight ahead, the open family room anchors the heart of the home. Steps away, a bright, efficient kitchen serves as a natural gathering point, complete with a cozy breakfast nook and a casual snack bar. Glass doors transition the indoor living out onto a sweeping wrap-around deck, inviting you to dine alfresco against the backdrop of the bay. This level is rounded out by a quiet sunroom and office that accesses an independent open balcony, alongside two spacious bedrooms and a versatile bonus room. The entire third floor is dedicated to a spectacular, private master oasis designed around its breathtaking environment. Massive windows wrap around the suite to capture the best waterfront vistas imaginable, allowing you to wake up to the sight of the bay from every angle before stepping out onto a private balcony. Custom decor elevates the tranquility of this top-level retreat, which features an adjoining spa-like bath and deep walk-in closets. Down on the ground level, multi-generational living or guest hosting is made effortless by a private fourth bedroom suite equipped with its own full bath. This level walks straight out to a screen-enclosed backyard resort, highlighted by a pristine pool and spillover spa. A covered lanai features year-round entertaining, situated next to a massive 3-car garage with oversized bays and built-in workshop space. Meticulously maintained with robust full stucco construction, a custom paver driveway, and a durable new roof, this remarkable property sits just steps from the historic trails of Philippe Park and minutes from the vibrant boutique shopping, cafes, and local festivals of downtown Safety Harbor. Offering an unparalleled blend of multi-generational accessibility, robust construction, and timeless coastal luxury, this Safety Harbor masterpiece represents a rare opportunity to own a piece of paradise. Schedule your private tour today to experience the ultimate Florida waterfront lifestyle firsthand. ROOF = 2025 / HVAC = 4 UNITS: 2011, 2018, 2019, 2025 / WATER HEATER = 2017

103 Royal Court, Safety Harbor

7957 2nd Avenue S, St Petersburg
$2,999,000
3 Beds ⋅ 4 Baths ⋅ South Cswy Isle 2nd Add SubDv. ⋅ 33707 Zip Code
Virtually Staged. JUST COMPLETED—2026 ELEVATED WATERFRONT LIVING IN SOUTH CAUSEWAY ISLE/YACHT CLUB ESTATES! From the moment you arrive, this distinctive waterfront residence makes an impression with its elevated design and custom hand-applied natural seashell exterior finish. Offering approximately 2,878 SF of heated and cooled living space with 3 bedrooms, 2 full baths and 1 half bath on the main living level, plus a separate den/office/bonus room that could be used as a 4th bedroom, the home provides exceptional flexibility. A striking custom-built stairway creates the transition to the elevated main living level and immediately showcases the home's craftsmanship. Combining natural wood with iron, stainless-steel supports and horizontal wire railings, the open architectural design makes the stairwell a feature of the residence rather than simply a passage between floors. Ascend to the main living level, where the home opens into a bright, expansive floor plan with kitchen, dining and living areas flowing together and drawing your attention toward the water. The kitchen features a large island, white cabinetry, quartz countertops and KitchenAid Signature Series stainless-steel appliances. LVP flooring continues throughout the living areas for a clean, contemporary coastal feel. The waterfront primary suite features a private balcony, large walk-in closet and luxurious bath with dual vanities, private toilet area and an oversized walk-in shower with marble walls. Additional bedrooms and baths provide comfortable accommodations for family and guests, while bathrooms on the main living level feature heated bidets. Moving toward the rear of the living space, this is where the home truly becomes about the Florida waterfront lifestyle. Step onto the expansive waterside deck, where stainless-steel posts and horizontal cable railings preserve the views. Below, an in-ground saltwater pool overlooks the water, while the private dock and two boat lifts with approximately 16,000-lb and 10,000-lb capacities put boating right outside your back door. Spend the day on the water, return for a swim and finish the evening watching the sunset from your backyard. The approximately 2,160 SF garage/lower level features a 5-car garage capable of accommodating up to 6 vehicles, epoxy flooring, an 8,000-lb automobile lift and separate half bath. A full-view glass rear garage door on the waterside provides convenient access for kayaks, paddleboards and other waterfront gear. Behind the finishes is substantial construction, including an engineered foundation with 33 pilings, engineered floor and roof trusses, PGT impact-resistant windows, impact-rated exterior doors, a 5V-crimp metal roof, engineered flood vents and breakaway construction. Located in South Causeway Isle/Yacht Club Estates, enjoy direct boating access to Boca Ciega Bay and the Gulf, world-famous beaches nearby and Downtown St. Petersburg approximately 20 minutes away for dining, museums, entertainment and professional sports. This is more than a waterfront home—it's an opportunity to live the boating, water and sunset lifestyle that makes this part of St. Petersburg so special. All dimensions are estimates and need to be verified by the buyer.

7957 2nd Avenue S, St Petersburg

786 59th Avenue Ne, St Petersburg
$739,900
3 Beds ⋅ 3 Baths ⋅ Edgemoor Estates SubDv. ⋅ 33703 Zip Code
Nearly new NE St Petersburg 2 story pool home in Edgemoor Estates subdivision. 3 bedrooms, 2 1/2 bathrooms 2 car garage with large bonus/game room on first floor (884 sq ft +/- 26x34) Perfect for an exercise, craft, hobby, party room or just needed extra storage space. Bring your most discerning detail oriented buyers to this CLEAN non smokers home that is immaculately maintained to a high standard. Never a pet inside since original construction in 2003. For those who entertain and enjoy their backyard, your friends and family will enjoy the inground pool & spa, pebble tec surface and covered BBQ area with an outside sink. Entertain in the lushly landscaped tropical setting. Fully vinyl fenced for privacy. Many new amenities to include new roof (2023) attic(s) are semi finished and insulated, new HVAC (2024) new luxury vinyl plank flooring throughout, modern kitchen with granite countertops and new Frigidaire Stainless Gallery series convection stove & refrigerator (2026). Deep water well for irrigation. Featuring high ceilings, wood burning fireplace and a large 2nd floor screened balcony. Security system is owned. Garage has epoxy coated floors and there is an extra side yard parking pad for a boat or RV. Hurricane modifications include impact windows, reinforced garage door, roof strapping and underground utilities (Electric&Water). Nearby community recreation includes the Mangrove Bay golf course, nature walks in Puryear Park rec center. Worldclass education is offered at Shorecrest Preparatory School or Canterbury School of Fl. Well located for access to downtown St Pete and area bridges. Flood insurance is assumable, current cost is $1600/yr! Show and sell! Wont last.

786 59th Avenue Ne, St Petersburg

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