Greenbriar Homes under $500,000

Greenbriar Homes under $500,000

Welcome to Greenbriar, a charming subdivision nestled in the heart of Florida, where community spirit and natural beauty come together to create an idyllic living environment. This vibrant neighborhood is perfect for families, young professionals, and retirees alike, offering a serene escape while still being conveniently located near the bustling attractions of the Sunshine State.

One of the most appealing aspects of Greenbriar is its diverse selection of homes, with many options available under $500,000. Whether you're looking for a cozy single-family home or a modern townhouse, Greenbriar has something to suit every taste and budget. These well-designed residences boast spacious layouts, inviting outdoor spaces, and the potential for personalization, making them ideal for anyone looking to create their dream home.

The subdivision is surrounded by lush greenery and picturesque landscapes, providing residents with ample opportunities for outdoor activities. Enjoy leisurely strolls through the neighborhood, take advantage of nearby parks, or spend weekends exploring the beautiful beaches just a short drive away. Greenbriar also features excellent amenities, including community pools, playgrounds, and walking trails that encourage an active lifestyle.

In addition to its stunning homes and amenities, Greenbriar is conveniently located near shopping centers, dining options, and top-rated schools, making it an ideal place for families to thrive. With its affordable housing options, friendly atmosphere, and prime location, Greenbriar is not just a place to live; it's a community where memories are made and dreams come true. Come discover your new home in Greenbriar today!

Newest Greenbriar Homes under $500,000

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
1822 Yoakum Street, Lehigh Acres
$290,000
4 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33972 Zip Code
Welcome to 1822 Yoakum Street in Lehigh Acres! This spacious 4-bedroom, 2-bathroom home offers an open-concept floor plan with plenty of room for comfortable everyday living and entertaining. Built in 2019, this home offers the peace of mind of newer major systems, including a newer roof, A/C, and water heater. The home also features a convenient two-car garage, screened-in patio, and pest control tubes built into the walls for easy ongoing pest management. One of the biggest advantages is the freedom of **no HOA**, giving you more flexibility without monthly association fees or the restrictions that can come with a planned community. Located in Lehigh Acres, this home offers a balance of space, convenience, and accessibility. The surrounding area is primarily residential, with nearby shopping, restaurants, parks, and everyday amenities throughout Lehigh Acres. Lehigh Acres Park and Veterans Park provide opportunities for recreation and outdoor activities, while shopping centers such as Lehigh Plaza are available for everyday errands. With its newer construction, spacious layout, no HOA, and convenient Lehigh Acres location, 1822 Yoakum Street is a great opportunity for anyone looking for a comfortable Florida home with room to make it their own.

1822 Yoakum Street, Lehigh Acres
2019 High Ridge Drive, Clearwater
$350,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
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
2400 Indigo Dr, Clearwater
$320,000
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
NEW ROOF! MOVE-IN READY! TONS OF NATURAL LIGHT! Welcome to Florida living at its best! This charming 2-bedroom, 2-bath home offers a comfortable layout, a 1-car garage, and a large corner lot with plenty of outdoor space. A standout feature is the spacious Florida room, filled with natural light and offering a wonderful flex space for relaxing, entertaining, a home office, hobby area, or simply enjoying the Florida sunshine year-round. The newer roof provides added peace of mind, while the property is located outside of a flood zone. The generous corner-lot setting offers additional privacy and room to enjoy the outdoors. Nature lovers will especially appreciate the neighborhood's resident peacocks, adding a unique touch to the Florida lifestyle. Whether you're looking for an affordable starter home, downsizing for retirement, or simply wanting a comfortable home base in sunny Clearwater, this property offers versatility and the opportunity to enjoy the relaxed Florida lifestyle. Two full bathrooms, a 1-car garage, abundant natural light, a newer roof, and a spacious Florida room make this home a great opportunity. *Buyer to verify if new owner must join Greenbriar HOA* Come see why this Clearwater home is ready to welcome you home!

2400 Indigo Dr, Clearwater
2040 Forest Drive, Clearwater
$449,970
2 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
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
402 Aberdeen Court N, Lakeland
$379,900
4 Beds ⋅ 3 Baths ⋅ Greenbriar SubDv. ⋅ 33813 Zip Code
Welcome to this well-maintained 4-bedroom, 2.5-bath home, ideally situated on a spacious .43-acre lot in a desirable in-town location with no HOA. Offering over-sized living spaces, an abundance of storage, and endless potential, this home provides the perfect opportunity to update at your own pace while enjoying a solid home with major improvements already completed. The floor plan features a formal living and dining room, perfect for entertaining or holiday gatherings, while the spacious family room offers a comfortable place to relax and opens through sliding glass doors to the 14' x 19' screened porch—an ideal spot to enjoy your morning coffee, unwind with a good book, or gather with family and friends while overlooking the expansive backyard. The kitchen offers warm wood cabinetry, generous cabinet and counter space, a casual dining area, and a convenient pass-through window overlooking the family room to keep everyone connected. The fourth bedroom is privately located just off the garage, making it an ideal space for guests, a home office, hobby room, or multigenerational living. A large laundry and utility room with a convenient half bath adds everyday functionality. The spacious primary suite features two closets and a private en-suite bath with a walk-in shower, while the additional bedrooms are all generously sized with ample closet space. Skylights brighten the bathrooms with natural light, and storage can be found throughout the home. Outside, you'll appreciate the side-entry two-car garage, oversized parking area, pull-down attic storage, mature landscaping, and attractive brick front exterior. Recent updates include a new roof (2024) and drainfield and septic system (2007). The A/C was replaced in 2010. Conveniently located near shopping, dining, medical facilities, parks, and major roadways, this home offers exceptional space, a fantastic location, and the opportunity to make it your own.

402 Aberdeen Court N, Lakeland
2050 High Ridge Drive, Clearwater
$240,216
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33763 Zip Code
AFFORDABLE HOUSING HOME.... NO INVESTORS. ONLY OWNER OCCUPIED ..SPECIAL REQUIREMENTS..Workforce housing property, land owned by Pinellas County Housing Authority, land lease contract required. Buyers must meet INCOME REQUIREMENTS of at or below a 120% of AMI based on household size. All income counts for anyone residing in the home. They must complete a Homebuyer Education course from the list. Mortgage must be for a leashold property. Spacious 3 bedroom, 2 bath, 1 car garage block home. Living area has a beautiful bay window, recessed lights and an area for a big tv screen. Updated baths. Double sinks in primary bath. Family room has french doors that lead to backyard with a shed for extra storage. Fenced yard. Property sold AS-IS. SOLAR PANELS ARE INCLUDED. OVER $20,000 Upgrade owner installed.

2050 High Ridge Drive, Clearwater
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
1964 Leghorn Street, Lehigh Acres
$324,900
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33972 Zip Code
Virtually Staged. Welcome to modern Florida living in the desirable Greenbriar area of Lehigh Acres. This beautifully crafted new construction home offers over 1,500 square feet of thoughtfully designed living space, featuring 3 bedrooms, 2 bathrooms, and a highly sought-after split-bedroom floor plan that perfectly balances privacy and functionality. Step inside to discover an open-concept layout enhanced by elegant tile flooring throughout, tray ceilings, and an abundance of natural light. The spacious living, dining, and kitchen areas seamlessly flow together, creating the ideal setting for both everyday living and entertaining. At the heart of the home, the chef-inspired kitchen showcases quartz countertops, soft-close cabinetry, a stylish tile backsplash, ample storage space, and modern finishes designed to impress. The oversized laundry room and abundant storage throughout the home provide both convenience and practicality. The private primary suite offers a relaxing retreat, while the generously sized guest bedrooms feature large closets rarely found in homes of this size. An epoxy-coated two-car garage adds durability and a polished finish to the home's impressive list of upgrades. Enjoy Florida's year-round outdoor lifestyle from both the welcoming front patio and the spacious rear patio overlooking the fully fenced backyard. A vacant lot to the left of the property provides additional privacy and open space, enhancing the home's peaceful setting. Combining quality craftsmanship, upscale finishes, and a desirable location, this move-in-ready new construction home delivers exceptional value and modern comfort in one of Lehigh Acres' growing neighborhoods.

1964 Leghorn Street, Lehigh Acres
1962 Leghorn Street, Lehigh Acres
$319,900
3 Beds ⋅ 2 Baths ⋅ Greenbriar SubDv. ⋅ 33972 Zip Code
Virtually Staged. Welcome to modern Florida living in the desirable Greenbriar area of Lehigh Acres. This brand-new construction home offers the perfect blend of thoughtful design, quality craftsmanship, and upscale finishes throughout. Featuring 3 bedrooms, 2 bathrooms, and just under 1,400 square feet of living space, the split-bedroom floor plan provides both privacy and functionality. From the moment you arrive, you'll appreciate the inviting front lanai and attractive curb appeal. Inside, elegant tile flooring flows seamlessly throughout the entire home, while soaring vaulted ceilings in the main living area create an open, airy atmosphere filled with natural light. The thoughtfully designed kitchen overlooks the spacious living and dining areas, making it ideal for both everyday living and entertaining. Showcasing modern cabinetry with soft-close doors and drawers, quartz countertops, a stylish tile backsplash, premium finishes, and ample prep space, this kitchen serves as the heart of the home. The private primary suite offers a true retreat, complete with a generous walk-in closet and a beautifully appointed en-suite bathroom featuring a large fully tiled walk-in shower designed with both style and functionality in mind. Designed for comfort and peace of mind, the home is equipped with hurricane-impact windows and doors throughout, providing enhanced security, energy efficiency, and storm protection. Step outside to the expansive under-truss rear lanai, offering the perfect space to enjoy Florida's year-round outdoor lifestyle, entertain guests, or simply unwind in your own backyard oasis. A privacy fence spans the rear property line, while the adjacent vacant lot to the right provides an added sense of openness and privacy rarely found in new construction communities. Additional highlights include a spacious 2-car garage with durable epoxy flooring, contemporary fixtures throughout, and all the advantages of brand-new construction with no updates or renovations needed. Move-in ready and built to impress, this exceptional Greenbriar residence combines modern design, premium finishes, and quality craftsmanship into a home that is as functional as it is beautiful. Whether you're searching for your first home, a seasonal Florida retreat, or an investment opportunity, this thoughtfully designed residence delivers style, comfort, and lasting value in one of Lehigh Acres' most desirable and rapidly growing neighborhoods.

1962 Leghorn Street, Lehigh Acres
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
Start Your Search