Greenbriar Homes under $500,000

Greenbriar Homes under $500,000

Welcome to Greenbriar, a delightful subdivision nestled in the heart of sunny Florida! This charming community offers an inviting atmosphere and a perfect blend of comfort and convenience, making it an ideal place for families, retirees, and everyone in between. With a variety of homes available for under $500,000, Greenbriar is an excellent choice for those seeking affordable living without compromising on quality or lifestyle.

As you stroll through the tree-lined streets of Greenbriar, you'll be captivated by the well-maintained homes that exude warmth and character. The subdivision features a diverse selection of properties, from cozy single-family homes to spacious townhouses, ensuring there’s something for everyone. With prices under $500,000, you can find the perfect abode that fits your budget while still enjoying the perks of Florida living.

Residents of Greenbriar enjoy easy access to a wealth of amenities, including nearby parks, shopping centers, and recreational facilities. The community is also conveniently located near major highways, making it simple to explore all that Florida has to offer—from stunning beaches to vibrant cultural attractions.

In addition to its prime location and affordable homes, Greenbriar fosters a strong sense of community. Neighbors often come together for local events, creating a friendly and welcoming environment for all. Whether you're looking to settle down or invest in a new property, Greenbriar is a community that promises a fulfilling lifestyle in the heart of Florida. Come discover the charm of Greenbriar, where your dream home awaits!

Newest Greenbriar Homes under $500,000

2580 Windwood Drive, Clearwater
$379,900
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv.
Well cared for and full of possibilities, this Greenbriar home is ready for your personal touch. Set on a corner lot in Clearwater’s established Greenbriar community, this well-cared-for 2-bedroom, 2-bath home pairs original character with room to make it your own. Built in 1974 with solid block construction, it offers 1,535 heated square feet and 2,154 total square feet, including a two-car garage—a hard-to-find bonus in Greenbriar...The original kitchen and bathrooms offer an opportunity to update to your taste, while the care this home has received is evident throughout. Settle in and plan improvements at your own pace, without feeling compelled to tackle every project at once. Both bathrooms are inside the home, and the air-conditioned Florida room provides a comfortable spot for reading, relaxing, or gathering. The two-car garage adds practical space for parking, storage, and projects, while the corner lot gives the property a distinctive presence. Bring your ideas—the next chapter is yours to design...Greenbriar residents enjoy a heated community pool, fitness room, and clubhouse with regular activities and events—all with a low HOA fee. Located approximately 8 miles from Clearwater Beach, this home puts white-sand beaches and spectacular sunsets within easy reach. Enjoy nearby Honeymoon Island State Park and the Dunedin Causeway for kayaking, fishing, and coastal recreation, or explore charming downtown Dunedin’s restaurants, boutiques, breweries, and community events. The Pinellas Trail, Clearwater Marine Aquarium, golf courses, Countryside Mall, hospitals, and a wide variety of dining options are also nearby. Baseball fans will appreciate access to Philadelphia Phillies and Toronto Blue Jays spring training games. Convenient access to both Tampa International Airport and St. Pete–Clearwater International Airport makes travel easy. Located in Flood Zone X, this Greenbriar home offers an inviting setting for a full-time residence or seasonal retreat, with plenty of ways to enjoy the Florida lifestyle…

2580 Windwood Drive, Clearwater

4130 Bayhead Drive Unit 105, Bonita Springs
$414,500
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv.
Perfectly positioned within the exclusive Greenbriar community, this first-floor residence captures sweeping views across the Bay Island golf course, protected wetlands, and the natural beauty that defines this sought-after setting. Offered turnkey furnished, the three-bedroom, two-bath condominium is filled with natural light and thoughtfully designed to maximize its picturesque surroundings. Expansive windows and an oversized screened lanai frame breathtaking northwestern sunsets and a tranquil backdrop of native birds and lush greenery. Inside, a warm organic-modern aesthetic blends neutral tones, rich wood accents, earthy textures, and clean lines to create a polished yet inviting atmosphere. A significant $80,000 kitchen renovation serves as the heart of the home, showcasing new appliances, updated flooring, and elevated finishes that enhance both style and functionality. The spacious layout offers a seamless flow for everyday living and entertaining, with interiors that feel both refined and comfortable. Designed with both beauty and peace of mind in mind, the residence features new impact-resistant windows and storm shutters on every window, providing enhanced protection and energy efficiency. A private under-building garage adds convenience and security. Greenbriar residents enjoy access to their own community pool and spa, tennis courts, and a newly constructed pavilion and pool house appointed with upscale finishes, a 75-inch television, and a resort-style atmosphere designed for year-round enjoyment. Beyond Greenbriar, Bonita Bay offers an unmatched lifestyle centered around nature, recreation, and waterfront living. Residents enjoy a brand-new private Gulf-front Beach Club with shuttle service, Backwater Jack’s restaurant, more than 12.5 miles of walking and biking paths, and a wide array of amenities including tennis, pickleball, bocce, basketball, canoeing, and kayaking. A full-service marina with Gulf access and boat storage options further enhances the coastal lifestyle. Optional memberships elevate the experience even further, offering access to five championship golf courses, a premier racquet center, and a state-of-the-art Lifestyle Center with fitness facilities and luxury spa services. Just outside the gates, The Promenade at Bonita Bay provides a vibrant destination for upscale shopping, dining, and social gatherings. Experience the perfect blend of elevated design, modern updates, and the exceptional lifestyle that defines Bonita Bay.

4130 Bayhead Drive Unit 105, Bonita Springs

2019 High Ridge Drive, Clearwater
$350,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv.
Welcome home to this charming 2-bedroom plus bonus room, 2-bath residence in the sought-after Greenbriar community! Offering a comfortable layout, abundant natural light, a one-car garage, and a beautifully fenced backyard, this home is designed for easy Florida living, relaxing, and entertaining. A new flat roof was installed in 2026, adding valuable peace of mind to this inviting home. Step inside and the kitchen greets you to the right, featuring abundant cabinetry, generous workspace, and room for a cozy breakfast table. The kitchen comes equipped with a full suite of appliances, including a built-in oven, stovetop, dishwasher, refrigerator, and convenient countertop microwave. A door from the kitchen provides easy access to the attached garage, where the washer and dryer are thoughtfully located for everyday convenience. The kitchen flows seamlessly into the spacious living and dining area, creating an inviting gathering space for both everyday living and entertaining. From here, step into the generously sized bonus room, where walls of windows showcase peaceful backyard views and bathe the space in natural light. Whether used as a family room, home office, hobby space, reading room, or entertaining area, this versatile room offers endless possibilities and a wonderful connection to the outdoors. Tucked away on the opposite side of the home, the bedrooms provide a sense of privacy and tranquility. The light and airy secondary bedroom features a well-sized wall closet and easy access to the nearby hall bath, complete with a classic tub and shower combination. A hallway linen closet with built-in shelving provides additional storage. The spacious primary bedroom offers a true retreat, with plenty of room to create your own private sanctuary. Enjoy the convenience of a private en suite bath and a generous walk-in closet with ample storage. Outside, the beautifully fenced backyard provides a private setting for morning coffee, weekend gatherings, gardening, or simply enjoying Florida's year-round sunshine. The home's thoughtful layout and bright living spaces make it easy to feel right at home. Located in the desirable Greenbriar community, residents enjoy access to a sparkling community pool and a welcoming neighborhood atmosphere. The central location puts shopping, dining, recreation, and everyday conveniences close at hand, while providing easy access for beach days and airport travel. With its versatile floor plan, abundant natural light, private backyard, community amenities, and new 2026 flat roof, this delightful Greenbriar home offers a wonderful opportunity to enjoy comfortable Florida living in a convenient location.

2019 High Ridge Drive, Clearwater

442 Windermere Drive, Lehigh Acres
$319,900
4 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv.
Seller is offering a 3% sales price credit towards mortgage rate buy down!!! Move in ready and built in 2024, this beautifully maintained 4 bedroom, 2 bathroom home at 442 Windermere Dr in Lehigh Acres offers the space, modern construction, and thoughtful layout today’s buyers are looking for. Set on a greenbelt with a private backyard, this home combines abundant natural light, a desirable split bedroom floor plan, impact windows and doors, and plank tile flooring throughout for an easy move in experience. Inside, the open living areas are filled with natural light and create a comfortable setting for everyday living and entertaining. The kitchen features a large island and connects seamlessly with the main living area, making it easy to stay connected whether you are cooking, dining, or relaxing. Plank tile flooring extends throughout the home, providing a clean, consistent look and eliminating the need to manage carpet. The split bedroom layout offers privacy for the spacious primary suite, which is positioned separately from the guest bedrooms. The primary bedroom provides plenty of room for a comfortable bedroom setup, while the ensuite bathroom features dual sinks and a walk in shower. The additional bedrooms are also generously sized and are conveniently located near the guest bathroom, making this layout ideal for those needing flexible living space. Large windows bring in plenty of natural light throughout the home while impact windows and doors provide an important combination of durability and storm protection. The attached 2 car garage adds everyday convenience and storage space. Step outside to enjoy the greenbelt setting and backyard, where mature oak trees add natural character and shade. There is also plenty of room to add a private pool, giving buyers the opportunity to create the outdoor space they want. With a 2024 construction date, modern finishes, four bedrooms, two bathrooms, a 2 car garage, split bedroom floor plan, impact windows and doors, plank tile flooring, greenbelt views, and room for a pool, this Lehigh Acres home is an excellent option for buyers searching for a move in ready home with modern construction

442 Windermere Drive, Lehigh Acres

2040 Forest Drive, Clearwater
$449,970
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv.
Welcome to this beautifully renovated 2-bedroom, 2-bathroom block home featuring 1,207 square feet of heated living space and a spacious 1.5-car garage. Nestled on a quiet, peaceful street surrounded by mature oak trees in Clearwater, this move-in-ready home has been thoughtfully updated with quality, comfort, and style in mind. Major improvements include a 2022 roof, fully paid-off solar panels installed in 2022 that convey with the sale, a brand-new 2026 HVAC system, a 2021 water heater, newer windows and doors, and much more. Step inside to discover two beautifully renovated bathrooms featuring stylish Moen and Delta plumbing fixtures. The brand-new kitchen with soft-close doors and drawers showcase elegant quartz countertops, new Samsung stainless steel appliances, modern finishes, and new light fixtures throughout. These extensive renovations create a fresh, clean, and contemporary atmosphere while preserving the warmth and comfort of home. Step outside and discover your private backyard oasis—a peaceful setting perfect for relaxing, entertaining, grilling, or enjoying Florida’s year-round outdoor lifestyle beneath the surrounding mature trees. Even better, this solid block-construction home is located in Flood Zone X, where flood insurance is typically not required by lenders. Airbnb and short-term rentals are permitted in the community, providing added flexibility for homeowners and investors. With a newer roof, paid-off solar panels, a new HVAC system, updated major systems, newer windows and doors, and extensive interior renovations, this home provides an exceptional combination of style, energy efficiency, comfort, and peace of mind. Conveniently located near shopping, dining, parks, beaches, and the many amenities and attractions throughout Pinellas County. Turnkey, beautifully updated, and ready for its new owner—schedule your private showing today! One or more photos have been virtually staged.

2040 Forest Drive, Clearwater

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