Greenbriar Homes with Pool Community Features

Greenbriar Homes with Pool Community Features

Welcome to Greenbriar, a picturesque subdivision nestled in the heart of Clearwater, Florida. This charming community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle.

Greenbriar is known for its inviting atmosphere and friendly neighbors, creating a warm sense of community that is hard to find elsewhere. The subdivision features beautifully landscaped streets lined with well-maintained homes, many of which boast private pools—perfect for those sunny Florida days when you want to relax and soak up the sun. Imagine stepping out of your back door and diving into your own oasis, a refreshing escape just steps away from your living room.

In addition to the stunning homes with pools, Greenbriar offers a variety of community amenities designed to enhance your living experience. Residents can enjoy access to well-kept parks, walking trails, and recreational facilities that promote an active lifestyle. Whether you prefer a leisurely stroll, a brisk jog, or a family picnic, the community has something for everyone.

Located in Pinellas County, Clearwater is renowned for its beautiful beaches, vibrant arts scene, and a plethora of dining and shopping options. With easy access to major highways and local attractions, Greenbriar residents enjoy the best of both worlds—serene suburban living and the excitement of city life.

Discover your dream home in Greenbriar, where community spirit thrives and every day feels like a vacation!

Newest Greenbriar Homes with Pool Community Features

2174 Scotland Drive, Clearwater
$478,900
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
Welcome to Greenbriar! This 3BR/2BA Clearwater home offers a wonderful opportunity to enjoy an established neighborhood, a convenient location, and a true Florida lifestyle. With a comfortable floor plan and plenty of potential to make the space your own, this home is ready for its next chapter. One of the highlights of living in Greenbriar is the community itself. Residents have access to the Greenbriar Club and community center, featuring a heated swimming pool, fitness and recreation spaces, shuffleboard, and a variety of activities and gathering areas. It’s a great place to stay active, meet neighbors, or simply relax and enjoy the Florida sunshine. The location puts you close to so much of what makes this area desirable, including charming Downtown Dunedin, shopping, dining, parks, golf, and the beautiful Gulf beaches.

2174 Scotland Drive, Clearwater
2580 Windwood Drive, Clearwater
$379,900
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
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
2040 Forest Drive, Clearwater
$439,970
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
LOCATION, LOCATION, LOCATION! 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
998 White Springs Lane, Winter Springs
$429,900
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 32708 Zip Code
Welcome home to this beautiful, move-in ready single-story residence situated in the highly desirable Greenbriar community in Winter Springs! Nestled along the manicured grounds near Tuscawilla Golf and Country Club, this updated 3-bedroom, 2-bathroom home features 1,587 sq. ft. of comfortable, functional living space with a 2-car attached garage. Major big-ticket improvements offer complete peace of mind, including a brand-new roof, new energy-efficient windows, a new water heater, and a 5-year-young HVAC system. Step inside to an inviting open layout filled with natural light and stylish upgrades throughout. The kitchen and bathrooms feature stunning quartz countertops, creating a fresh, modern aesthetic that makes daily living and entertaining a joy. The primary bedroom serves as a peaceful retreat complete with an updated private en-suite bathroom, while two additional spacious bedrooms offer perfect flexibility for guest quarters, a nursery, or a dedicated home office. Outside, enjoy a low-maintenance lot with mature landscaping and beautiful community surroundings. The Greenbriar neighborhood features tree-lined streets, a community park, and a sparkling pool—all zoned for top-rated Seminole County schools (Rainbow Elementary, Indian Trails Middle, and Winter Springs High). Conveniently located near shopping, dining, parks, and major roadways, this turn-key property is completely ready for its new owners—schedule your private showing today!

998 White Springs Lane, Winter Springs
2373 Forest Drive, Clearwater
$344,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
Virtually Staged. $5,000 SELLER-PAID RATE BUYDOWN AVAILABLE! Ask how you may be able to lower your first-year monthly mortgage payment... Clearwater living with the big-ticket updates already done! Located in the Greenbriar community, this solid block 2-bedroom, 2-bath home with an oversized 1-car garage combines classic Florida character with an impressive list of improvements. One of the home's standout features is the beautifully polished terrazzo flooring that flows throughout the living areas. Prized for its exceptional durability, longevity, and easy maintenance, terrazzo is a timeless feature found in many classic Florida homes. Recently polished to bring back its natural beauty and shine, these floors add character while offering a hard-wearing surface designed to last for decades. A large picture window fills the living room with natural light, creating a bright and inviting space. The home has been freshly painted inside and out and features modern lighting, impact-resistant windows, a newer HVAC system with all new ductwork, and an updated kitchen with new Whirlpool appliances. The kitchen cabinetry is approximately eight years old. The tile roof was installed in 2012 and includes a secondary water barrier. The floor plan offers two bedrooms and a full bathroom inside the home, plus a second full bathroom with a shower located in the oversized garage. Outside, enjoy a screened patio with a ceiling fan, tropical landscaping, and a fully fenced backyard with a separate dog run and divided outdoor spaces. Greenbriar amenities include a heated community pool, fitness room, clubhouse, and community activities, all with a low HOA fee. The home is located in Flood Zone X, approximately 8 miles from Clearwater Beach, and convenient to downtown Dunedin, shopping, dining, golf, Countryside Mall, and Phillies and Blue Jays Spring Training. Solid block construction, impact windows, tile roof, newer HVAC, updated kitchen, and beautifully restored terrazzo floors. Come see the value and character this Greenbriar home has to offer!

2373 Forest Drive, Clearwater
2061 Fair Oak Drive, Clearwater
$409,900
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
Welcome to this well-maintained 3-bedroom, 2-bathroom home in the Greenbriar community of Clearwater, offering a recently updated kitchen, a 2018 HVAC system, and a spacious driveway. This home is move-in ready and designed for everyday convenience. The open-concept living room and kitchen create an inviting space for gathering with family and friends. The beautifully updated kitchen features quartz countertops, stainless steel appliances, a farmhouse sink, floating shelves, a large peninsula with seating, and a brand-new dishwasher installed in 2026. Wood-look luxury vinyl plank flooring flows throughout the main living areas, adding warmth and durability. The spacious primary features a wall-to-wall closet and ceiling fan, while the third bedroom is equipped with a built-in Murphy bed and additional storage, making it an ideal guest room, home office, or flexible living space. The main bathroom features a tub/shower combination, and the enclosed Florida room with newer windows provides additional living space perfect for relaxing, entertaining, or enjoying the Florida sunshine year-round. For added peace of mind, the home includes a Ring Security system featuring a wired front spotlight camera, rechargeable backyard camera, rechargeable Ring video doorbell, and interior plug-in chime. A portion of the original garage had been previously converted into additional living space, providing increased flexibility. The remaining garage area still offers enough room for a golf cart, storage, tools, or convert back to a full garage, giving you the best of both worlds. Greenbriar residents enjoy a low HOA while taking advantage of outstanding community amenities, including a heated swimming pool, fitness room, active clubhouse, and a variety of social activities and events. Conveniently located just minutes from Countryside Mall, Whole Foods, popular restaurants, shopping centers, and everyday conveniences, this home also offers a quick drive to the beautiful Gulf beaches. Schedule your showing today!

2061 Fair Oak Drive, Clearwater
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