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 in Pinellas County offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle close to the vibrant Gulf Coast.

Greenbriar is renowned for its beautifully designed homes, many of which feature private pools that invite you to relax and unwind under the Florida sun. Imagine starting your day with a refreshing dip, or hosting summer barbecues in your own backyard oasis. The pool community aspect of Greenbriar fosters a sense of camaraderie among neighbors, as residents often gather around their pools for casual get-togethers, creating lasting friendships and cherished memories.

Beyond the allure of the homes, Greenbriar boasts an array of community features that enhance the living experience. Residents can enjoy well-maintained green spaces, walking paths, and recreational areas, perfect for leisurely strolls or energetic outdoor activities. The community also hosts various events throughout the year, allowing residents to connect and engage with one another.

Greenbriar’s prime location in Clearwater means you’re just a stone’s throw away from stunning beaches, shopping centers, and an array of dining options. With easy access to major highways, you can explore everything that the beautiful Gulf Coast has to offer.

If you’re looking for a welcoming community with fantastic homes and the added luxury of a pool, Greenbriar is the perfect place to call home. Come and experience the charm of this delightful subdivision today!

Newest Greenbriar Homes with Pool Community Features

2066 Hillwood Drive, Clearwater
$439,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
A sparkling saltwater pool completed in 2025, a beautifully tiled patio, gleaming polished terrazzo floors, and a remodeled kitchen make this Greenbriar home anything but ordinary. Lovingly remodeled and maintained, this home has so many thoughtful details to appreciate. The tropical front landscaping sets a relaxed Florida tone, while the fully fenced backyard is absolute perfection—a private, low-maintenance retreat designed for enjoying the sunshine instead of spending every weekend on yardwork. Inside, the welcoming open floor plan features two bedrooms, one full bathroom, and a finished Florida room that provides additional flexible space. The original terrazzo floors have been professionally refinished and polished, and vinyl plank flooring complements the Florida room. The kitchen has been remodeled, and the main bathroom was remodeled in 2017, including associated plumbing updates. The attached one-car garage includes a remodeled bathroom with a toilet and shower, as well as a utility sink. The backyard is the showstopper. Completed in February 2025, the saltwater pool features a pebble-style finish and mother-of-pearl-style accent tile along the steps and pool edge. The tiled pool deck and patio provide plenty of room for lounging and entertaining, while artificial turf keeps maintenance simple. The yard also includes a new shed, a backyard sprinkler system installed in 2025, irrigation for the garden area, and pool equipment. The pool is not heated or screened, and its warranty is not transferable. Important improvements include a roof replaced in September 2019, HVAC replaced in April 2019, complete ductwork replacement in October 2026, a water heater replaced in March 2018, and exterior paint completed in 2020. The well and front-yard sprinkler system were installed in 2022, with the backyard sprinkler system added in 2025. Greenbriar offers a heated community pool, fitness room, clubhouse, and community activities with affordable annual fees. The home is in Flood Zone X and is convenient to Countryside Mall, shopping and dining along US 19 and State Road 580, downtown Dunedin, Clearwater Beach, and Gulf Coast recreation. Baseball fans can also enjoy spring training in Clearwater and Dunedin. There are so many details to appreciate in this beautifully maintained home, and the backyard truly must be experienced in person. Schedule your showing and come see the pool, patio, polished terrazzo floors, and inviting Florida lifestyle for yourself.

2066 Hillwood Drive, Clearwater
2013 Forest Drive, Clearwater
$375,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
Pride of Ownership Shines | Beautifully Maintained Clearwater Home | Impact Windows | Community Pool From the moment you arrive at 2013 Forest Drive, you’ll immediately notice the pride of ownership that has gone into this beautifully maintained 2-bedroom, 1.5-bath home. From the meticulously cared-for landscaping to the inviting interior, this is a home that has truly been loved. Step inside and enjoy a comfortable, welcoming floor plan highlighted by a remodeled kitchen featuring granite countertops, attractive cabinetry, and plenty of space for everyday living and entertaining. One of the home's major advantages is the addition of impact-resistant windows, providing extra protection, energy efficiency, and peace of mind. Outside, the beautifully maintained landscaping creates impressive curb appeal, while a deep well provides water for the landscaping, helping reduce the expense of keeping the property looking its best. In the rear of the home, the screened patio provides the perfect place to enjoy your morning coffee, relax with a good book, or unwind at the end of the day while enjoying Florida's year-round outdoor lifestyle. When it's time to cool off, take advantage of the community clubhouse and swimming pool—perfect for enjoying those warm Florida days, meeting neighbors, and taking advantage of the community lifestyle. Meticulous landscaping. Impact windows. Remodeled kitchen. Screened outdoor living. Community amenities. This is more than just a house—it's a home that reflects years of care and pride of ownership. Schedule your private showing and come see why 2013 Forest Drive deserves to be at the top of your list.

2013 Forest Drive, Clearwater
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
$369,900
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
$429,970
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! Big-ticket updates, classic Florida character, and Greenbriar community amenities! This solid block Clearwater home offers 2 bedrooms, 2 full bathrooms (including one in the garage), an oversized 1-car garage, and beautifully polished terrazzo floors that bring timeless character to the living spaces. A large picture window fills the living room with natural light, while fresh interior and exterior paint give the home a refreshed look. Major improvements include impact-resistant windows, a new HVAC system with all-new ductwork, and a tile roof installed in 2012 with a secondary water barrier. The updated kitchen features new Whirlpool appliances, and the interior bathroom has a new vanity.The home offers 904 square feet of heated living space and 1,410 total square feet. Inside are two bedrooms and one full bathroom, while a second full bathroom with a shower is conveniently located in the garage. It's a practical layout with a little extra flexibility, whether you're coming in from gardening or spending time outdoors. Step outside to a newly screened patio with a ceiling fan, a comfortable spot for morning coffee or relaxing at the end of the day. The fully fenced backyard features divided outdoor areas, tropical landscaping, and an additional concrete pad for grilling, outdoor seating, or storage. Well points are also in place for irrigation.Greenbriar offers a heated community pool, fitness room, clubhouse, and community activities, all with low HOA fees. The home is located in Flood Zone X and combines desirable updates with the appeal of an established Clearwater community. Conveniently situated near shopping, restaurants, golf courses, and Countryside Mall, with access to downtown Dunedin, Clearwater Beach, and the Gulf Coast. Baseball fans can also enjoy nearby spring training attractions for the Philadelphia Phillies and Toronto Blue Jays.With its polished terrazzo floors, substantial improvements, inviting outdoor spaces, and community amenities, this Greenbriar home is worth seeing in person. Schedule your showing today!

2373 Forest Drive, Clearwater
240 E Glassboro Court Unit 4A, Hernando
$145,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 34442 Zip Code
Welcome to easy, maintenance-free living in one of Citrus County’s most established communities! This charming 2-bedroom, 2-bathroom condo in Citrus Hills includes a personal carport and is just steps from the community pool. Inside, tile flooring runs throughout, and the vaulted ceiling with skylight fills the main living area with natural light. The galley-style kitchen features stainless steel appliances, dark cabinetry, and generous counter space. The open living and dining areas create an airy feel, while the primary suite offers a walk-in closet and private bath. A dedicated laundry room adds everyday convenience, and the roof was replaced in 2022 for added peace of mind. Relax on the front patio with your morning coffee or unwind in the enclosed lanai overlooking the serene rear setting, perfect for quiet evenings or entertaining guests. Condo fees include cable, WiFi, water, sewer, and trash, making budgeting simple and stress-free. Whether you’re looking for a full-time residence, seasonal retreat, or smart investment, this home checks the boxes. Just minutes from the Shoppes at Black Diamond (Target, Aldi, Texas Roadhouse, Starbucks) with Sprouts, BJ’s, Planet Fitness, LongHorn Steakhouse, Dick’s Sporting Goods and more coming in 2026 — plus the future Tampa General Hospital. Quick access to the newly improved Hwy 589 puts Tampa International Airport within easy reach. Don’t miss your opportunity to own in the heart of Citrus Hills — schedule your showing today!

240 E Glassboro Court Unit 4A, Hernando
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