Location: Greenbriar, Clearwater
Do Not Show Listings
2171 SCOTLAND DR, CLEARWATER, FL 33763
$375,00058 Days on yellowkey MLS ID: TB8492471
1 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1109 Built: 1971Monthly Fee: $18 Tax: $2,438 (2025)Community: GreenbriarSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,438
Elementary School: Garrison-Jones Elementary-PN
High School: Dunedin High-PN
Tax Year: 2025
Middle School: Safety Harbor Middle-PN
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained three-bedroom, two-bathroom home in the desirable Greenbriar community of Clearwater, where comfort and convenience come together. From the moment you arrive, you’ll appreciate the one-car garage and oversized driveway, offering ample parking for guests. Step inside to a light and bright interior featuring an open floor plan designed for both everyday living and entertaining. The home showcases engineered hardwood flooring, elegant crown molding, and a seamless flow between the living room, dining area, and kitchen. The open kitchen is a true centerpiece, complete with stainless steel appliances, granite countertops, and plenty of cabinetry - perfect for preparing meals while staying connected with family and guests. A split floor plan provides added privacy, with the spacious primary suite tucked away from the secondary bedrooms. The primary bedroom features ceiling fans for added comfort and sliding glass doors leading to the enclosed sunroom. The en-suite bathroom is thoughtfully designed with accessibility features, making it walker and wheelchair friendly. The additional bedrooms are nicely sized and share a well-appointed full bathroom with a granite countertop vanity and tub/shower combination. Enjoy year-round relaxation in the enclosed sunroom, complete with its own mini AC unit to keep the space cool and comfortable while offering peaceful views of the fenced backyard. Step outside to your private outdoor oasis featuring a covered paver patio, perfect for outdoor dining, grilling, gardening, or simply unwinding. Ideally located just minutes from Countryside Mall, you’ll have easy access to shopping, dining, and entertainment. Plus, the stunning Gulf beaches are just a short drive away, allowing you to enjoy the very best of Florida living. This move-in ready home offers the perfect blend of functionality, charm, and location - don’t miss your opportunity to make it yours!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
2451 RUTLAND LN, CLEARWATER, FL 33763
$454,00024 Days on yellowkey MLS ID: TB8505300
REDUCED by $15,900 (3.4%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1416 Built: 1968Monthly Fee: $18 Tax: $6,402 (2025)Community: Greenbriar Unit 6-BSingle Family
Taxes:$6,402
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Take advantage of a valuable opportunity with a Seller credit of up to $5,000 toward the Buyer’s allowable closing costs, prepaid expenses, discount points/rate buydown, and/or other lender-approved costs at closing. This generous incentive can help reduce your upfront expenses and make homeownership even more affordable. A fantastic opportunity for Buyers looking to maximize savings and flexibility!NOT IN A FLOOD ZONE! Welcome to effortless Florida living in the highly desirable Greenbriar community! This beautifully updated 3-bedroom, 2-bath home with a 1-car garage offers the perfect blend of modern style and everyday comfort. Step inside and immediately appreciate the thoughtful upgrades throughout, including durable waterproof laminate flooring, elegant wall molding, and custom panel accents that bring warmth and character to the space. The kitchen is truly the heart of the home, featuring sleek shaker-style cabinetry, stunning quartz countertops, and ample space to cook, gather, and entertain. Enjoy peace of mind with major 2024 updates, including a new A/C system and hot water heater. Outdoors, you’ll find a fully fenced backyard—perfect for relaxing, pets, or entertaining—along with an enclosed porch that offers versatile bonus space ideal for a home office, lounge, or hobby area. With a low HOA of just $210/year, Greenbriar residents enjoy access to fantastic amenities, including a community pool, fitness center, and recreational facilities. Ideally located near Dunedin, top-rated shopping and dining, and just a short drive to Clearwater Beach, this home delivers the perfect combination of convenience and coastal lifestyle. Don’t miss your opportunity—schedule your private showing today and experience all this exceptional home has to offer!
Listing is courtesy of: BILTMORE GROUP INC (727-559-2008)
Listing Agent: Juliana Fenno (727-688-1895)
2542 WYNNEWOOD DR, CLEARWATER, FL 33763
$389,90027 Days on yellowkey MLS ID: TB8504418
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1220 Built: 1973Monthly Fee: $18 Tax: $5,286 (2025)Community: GreenbriarSingle Family
Taxes:$5,286
Remarks: Gorgeous 2-bedroom, 2-bath home featuring an updated, open, light and bright floor plan! From the moment you step inside, you’re welcomed by an abundance of natural light, stunning luxury vinyl plank flooring throughout, and a show-stopping kitchen that opens seamlessly to the main living space. The kitchen is truly the heart of the home, boasting a massive island with granite countertops, updated cabinetry, stainless appliances, a butcher block accent counter, and a prime location between the living/dining room combination and a versatile bonus room. Both bedrooms are generously sized, with the primary suite offering an en-suite bath complete with a walk-in shower and dual built-in cabinets. Sliding glass doors lead to a covered back patio overlooking an oversized, fully fenced backyard with double gates—perfect for storing boats, trailers, or other toys. The widened driveway provides ample parking for multiple vehicles leaving plenty of room to spare. Major updates include a BRAND-NEW (2026) ROOF, (2021) hot water heater, and (2016) HVAC system. Located in a high and dry NON-FLOOD zone, this home is just minutes from Dunedin, Honeymoon and Caladesi Islands. Community amenities INCLUDE a pool, clubhouse, shuffleboard courts, and a fitness room, all with a low HOA fee. Enjoy easy access to Clearwater and Dunedin beaches, shopping, dining, and the vibrant downtown Dunedin area. Tampa International Airport is approximately 30 minutes away. Move-in ready and perfect as a primary residence or seasonal retreat—don't wait, this opportunity won't last long. Call TODAY!
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Amanda Justus (727-330-4478)
2001 GREENBRIAR BLVD #13, CLEARWATER, FL 33763
$64,900146 Days on yellowkey MLS ID: W7881767
REDUCED by $5,000 (7.2%) on 05/16/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 605 Built: 1970 Tax: $1,129 (2024)Community: Greenbriar CondoSpa: NoCondo
Taxes:$1,129
Tax Year: 2024
Remarks: Updated one-bedroom, 1 Bath, 55+ 2nd Story Condo in Clearwater, featuring 8-foot-plus ceilings and crown molding for a clean, upscale finish. This residence delivers the feel of executive living at a fraction of the typical cost. Inside, you’ll find brand-new kitchen appliances, new flooring throughout, and a fully updated bathroom—with no carpet anywhere in the home. The laundry room is conveniently located just steps away, adding to the effortless lifestyle this property provides. Enjoy peace of mind knowing the home is located in a non-flood zone, per the County and let the community amenities elevate your everyday living. The beautiful pool and clubhouse create a resort-like atmosphere, while the scenic walking along a tranquil creek offers a relaxing retreat right outside your door. There’s no yard work, no roof maintenance, no mowing, and no weeds to pull—just lock-and-leave convenience paired with comfort and style. This is low-maintenance living at its finest, perfect for those who value quality, simplicity, and a polished lifestyle, the HOA also covers Cable TV & Internet & Sewer & Trash & Water & Fitness Center & Pool & Clubhouse. Less than 20 miles to St. Pete Beach In Florida was just named The #1 Beach in America and the Fifth Best Beach in The World. Please view two videos: Tour 1 & Tour 2
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Eric Jenkins, Pa (727-409-3484)
2063 PINE RIDGE DR, CLEARWATER, FL 33763
$374,90075 Days on yellowkey MLS ID: TB8487303
REDUCED by $9,100 (2.4%) on 05/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1158 Built: 1962Monthly Fee: $23 Tax: $4,547 (2025)Community: GreenbriarSingle Family
Taxes:$4,547
Remarks: Welcome to the ever-popular Greenbriar community in Clearwater, where the Florida lifestyle is not just a dream, it’s your everyday reality. This charming 2-bedroom, 2-bathroom block home with a 1-car garage is move-in ready and perfectly positioned to enjoy everything the Gulf Coast has to offer. Short-term rentals such as Airbnb are allowed, offering flexibility for owners and potential income opportunities. From the moment you arrive, the covered front porch offers a warm welcome and the perfect spot to relax with your morning coffee. Inside, the home features a bright and comfortable living and dining room combination, creating an open and inviting space for everyday living or entertaining. The beautifully remodeled kitchen is both stylish and functional with bright white cabinetry, butcher block countertops, stainless steel appliances, and a cozy breakfast nook area. Just beyond the dining room is the enclosed Florida room, a versatile space that can easily serve as a den, playroom, office, or additional living area. A convenient breakfast bar connects this space to the kitchen, making it ideal for casual meals or conversation while cooking. Down the hallway you’ll find two comfortable bedrooms including a spacious primary bedroom along with the main hall bathroom. In the garage, a second full bathroom offers a thoughtful and practical feature, especially after a day at the beach. With the washer and dryer located here as well, it’s the perfect place to rinse off the sand and toss in beach towels and bathing suits before heading back inside. Step outside to enjoy the nicely paved brick patio overlooking a good-sized fenced backyard, ideal for relaxing evenings, weekend barbecues, or letting pets roam freely. Recent updates include a newer remodeled kitchen, interior and exterior paint, a water heater installed in 2018, a newer electrical panel in 2020, and a brand-new irrigation pump. Greenbriar residents enjoy access to a heated community pool, fitness room, and an active clubhouse with regular activities and events. The HOA remains low while still offering great amenities. Location is everything, and this home truly delivers. Just about 8 miles from Clearwater Beach and other stunning Gulf beaches, you’ll be close to soft white sand and spectacular sunsets whenever the mood strikes. Enjoy a short drive to charming downtown Dunedin, nearby aquariums, golf courses, Countryside Mall, hospitals, and a wide variety of restaurants. Baseball fans will love being near Spring Training games for both the Philadelphia Phillies and the Toronto Blue Jays. Best of all, the property is located in a non-flood zone. Whether you're looking for a full-time residence, a winter retreat, or an opportunity to generate rental income while enjoying the best of Florida living, this Greenbriar home offers comfort, convenience, and endless opportunities for fun just minutes from the beach.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Vivian Resnick (813-410-2890)
2019 HIGH RIDGE DR, CLEARWATER, FL 33763
$345,000113 Days on yellowkey MLS ID: TB8472105
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1481 Built: 1966Monthly Fee: $18 Tax: $1,037 (2024)Community: GreenbriarSingle Family
Taxes:$1,037
Remarks: Welcome home to this charming 2-bedroom plus bonus, 2-bath residence with a one-car garage and a beautifully fenced backyard, perfect for relaxing or entertaining. Upon entering, the kitchen greets you to the right, offering abundant cabinetry, space for a cozy breakfast table, and a full suite of appliances including a built-in oven, stovetop, dishwasher, and refrigerator as well as a counter top microwave. The kitchen also provides convenient access to the garage, where the washer and dryer are thoughtfully located. Flowing seamlessly from the kitchen is a spacious living and dining area designed with both comfort and gatherings in mind. This inviting space opens into a generously sized bonus room surrounded by walls of windows that frame serene backyard views and fill the home with natural light—an ideal spot for morning coffee, evening unwinding, or hosting friends and family. Tucked away on the opposite side of the home, the sleeping quarters offer privacy and tranquility. The secondary bedroom is light and airy with a well-sized wall closet, while the nearby hall bath features a classic tub and shower combination. A hallway linen closet with built-in shelving adds extra storage and convenience. The primary bedroom is a true retreat, boasting a spacious layout, a private en suite bath, and a generous walk-in closet. Nestled within the sought-after Greenbriar community, residents enjoy access to a sparkling community pool and a welcoming neighborhood atmosphere. With its thoughtful layout, bright living spaces, and inviting outdoor setting, this home offers the perfect blend of comfort and charm. This community is located close to shopping, dining, recreation and easy travels to the beach and/or the airport - this central location makes access to every super easy!
Listing Agent: Vanessa Leonard (727-647-2706)
2132 GREENBRIAR BLVD, CLEARWATER, FL 33763
$359,00012 Days on yellowkey MLS ID: TB8509507
0 Days Off yellowkey (back on 5/22/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1786 Built: 1970 Tax: $1,824 (2025)Community: Greenbriar Unit 6-ASingle Family
Taxes:$1,824
Remarks: Under contract-accepting backup offers. This home is in a great location and has been beautifully maintained! Come inside this 2-bedroom, 2-bath home located in the highly desirable Greenbriar community of Clearwater. Designed for comfort and convenience, this move-in ready home is ideal for full-time residents, seasonal homeowners, or anyone seeking a relaxed, low-maintenance lifestyle in a prime location. Inside, you’ll find a bright and inviting open-concept living and dining area filled with natural light. The spacious kitchen offers ample cabinetry and generous counter space, flowing easily into the dining area. Each bedroom is comfortably sized, while the primary suite features its own private en-suite bath for added comfort and privacy. Outside, the established yard provides more time to enjoy everything Florida. Conveniently situated just minutes from Downtown Dunedin, Countryside Mall, and the beautiful sand of Clearwater Beach, this home also offers quick and easy access to Tampa and St. Petersburg, tons of shopping, dining, parks, and recreation within just a few minutes! This one is a must see!
Listing is courtesy of: RENTTHEBAY.COM (813-875-7368)
Listing Agent: Mike Hooper (813-597-1715)
2040 FOREST DR, CLEARWATER, FL 33763
$350,000108 Days on yellowkey MLS ID: TB8463647
0 Days Off yellowkey (back on 5/16/2026)
REDUCED by $20,000 (5.4%) on 05/04/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1207 Built: 1971Monthly Fee: $12 Tax: $5,943 (2024)Community: GreenbriarSpa: NoSingle Family
Taxes:$5,943
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. SIGNIFICANT PRICE REDUCTION. Bring all offers. Incredible opportunity for buyers. This special home is an easy-to-turn-key rental or single-family home. Solar panels installed in 2021 and are fully paid for, keeping electric bill very low! The front door opens to a large living room, open to kitchen and dining area. The kitchen is beautifully updated with a huge island with storage, quartz counters, brand new dishwasher and disposal. Newer laminate floors plus new carpet in bedrooms! The primary bedroom has a walk-in closet and an ensuite bath. The Florida room is a great space for a family room, gym or playroom and has its own AC/Heat window unit. Yard has mature landscaping and an irrigation system. Oversized one-car garage. Newer roof, HVAC, water heater, and newer vanity in primary bath. Newer windows in the home. The Greenbriar community offers a clubhouse, heated pool, fitness center, library, game room and shuffleboard courts.
Listing is courtesy of: KELLER WILLIAMS SOUTH TAMPA (813-875-3700)
Listing Agent: Martha Vancamp (757-560-3515)
2337 BLACK OAK LN, CLEARWATER, FL 33763
$410,00015 Days on yellowkey MLS ID: TB8509020
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1073 Built: 1964 Tax: $5,888 (2024)Community: GreenbriarSpa: NoSingle Family
Taxes:$5,888
Remarks: Charming, upgraded concrete-block home in flood zone X (no damage from Helene or Milton). This low-maintenance property offers impressive upgrades and features: Newer mini-splits in the master bedroom and Florida room , 2024 whole-house water softening and filtration system, a 2024 50A generator inlet that includes a 11 KW portable GENERATOR which powers the entire home (central A/C has a soft-start kit to run smoothly on generator power). This home is complete with IMPACT WINDOWS! The Florida room is ideal as a home office! The home also features a modern kitchen, bathrooms, flooring, low-maintenance front yard, an irrigated rear yard with a French drain system for stormwater, and a unique LANAI!. Great proximity to downtown Dunedin AND downtown Safety Harbor. Great house. Great location. Great Florida living.
Listing is courtesy of: MIHARA & ASSOCIATES INC. (813-960-2300)
Listing Agent: Gregory Silvestro (813-263-8723)
2561 BLACKWOOD CIR, CLEARWATER, FL 33763
$400,00057 Days on yellowkey MLS ID: TB8492045
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1322 Built: 1973Monthly Fee: $18 Tax: $6,929 (2025)Community: GreenbriarSingle Family
Taxes:$6,929
Remarks: Welcome to this charming and whimsical 2-bedroom, 2-bathroom (with bonus room) single-story home in Clearwater, Florida! Nestled in a quiet, private neighborhood, this home offers sweet upgrades, warm Florida color scheme, and flexible to make it your own. There is a clubhouse with an amazing pool, gym and fun offerings to participate in (and even resident peacocks). Conveniently located to the beautiful shores of Clearwater Beach and all the great surrounding towns like Dunedin, Gulfport, St Petersburg. Blocks away from a nature trail and close to shopping and dining at Countryside Mall. Inside, you’ll find a bright layout with a modern kitchen featuring stainless steel appliances and granite countertops. A versatile bonus room provides the perfect opportunity to convert into a third bedroom, office, or additional living space. Step outside to enjoy a screened-in lanai and a fully fenced backyard— great for pups! This home offers the perfect blend of peaceful living and coastal convenience. Don’t miss this opportunity to own a warm and inviting home in a prime location! Seller is willing to rent out the property starting July 1st.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Samantha Cline (941-962-6944)
2124 GREENBRIAR BLVD, CLEARWATER, FL 33763
$379,00032 Days on yellowkey MLS ID: TB8502677
REDUCED by $10,000 (2.6%) on 05/15/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1119 Built: 1966 Tax: $2,240 (2025)Community: Greenbriar Unit 6-ASingle Family
Taxes:$2,240
Remarks: Welcome to your move-in ready Clearwater retreat! Nestled in the sought-after Greenbriar community, this well-maintained 2-bedroom, 2-bath home combines modern comfort with classic Florida charm. Perfect for downsizers, snowbirds, or year-round residents seeking a low-maintenance lifestyle, this residence offers an ideal blend of convenience, efficiency, and location. Step inside to find a bright, open living and dining area with abundant natural light and neutral finishes that complement any style. The kitchen features plenty of cabinetry and workspace, opening seamlessly to the dining area—perfect for casual meals or entertaining. Both bedrooms are generously sized, and the primary suite includes an en suite bath for added privacy. Enjoy peace of mind with a brand-new HVAC system and ductwork installed in 2023, ensuring energy efficiency and comfort throughout the seasons. The low-maintenance yard allows you more time to enjoy Florida living—whether it’s relaxing in your screened porch, visiting the community clubhouse, or exploring nearby attractions. Located minutes from Downtown Dunedin, Countryside Mall, world-famous Clearwater Beach, and just a short drive to both Tampa and St. Pete, this home offers unbeatable access to dining, shopping, and recreation. Residents of Greenbriar enjoy a friendly, established neighborhood with optional community amenities, including a pool and fitness center—without the high monthly fees. Key Features: 2 Bedrooms | 2 Bathrooms | 1-Car Garage New AC & Ductwork (2023) Low Maintenance Landscaping Light, Open Floor Plan Prime Clearwater Location Close to Beaches, Shopping & Parks Optional HOA Amenities Move-in ready, exceptionally well-cared-for, and ideally located—2124 Greenbriar Blvd represents the best of easy Florida living.
Listing is courtesy of: VREELAND REAL ESTATE LLC (904-347-7690)
Listing Agent: Kris Nelson (503-997-4754)
2161 NE HILLWOOD CT, CLEARWATER, FL 33763
$475,00035 Days on yellowkey MLS ID: TB8501733
1 Days Off yellowkey (back on 5/15/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1587 Built: 1972Monthly Fee: $18 Tax: $2,937 (2025)Community: GreenbriarSpa: NoSingle Family
Taxes:$2,937
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Completely renovated from top to bottom, this stunning spacious 3 bedroom 2 bath home offers modern living in a peaceful, family-friendly setting. Nestled on a quiet cul-de-sac in beautiful neighborhood, the property features mature landscaping that provides both beauty and privacy. Step inside to discover a stunning mid century modern kitchen designed to impress, complete with elegant quartz countertops, updated cabinetry, stainless steel appliances, and high-end finishes—perfect for both everyday living and entertaining. The home also boasts newly installed hurricane-impact windows, offering enhanced safety, energy efficiency, and peace of mind. Every detail has been thoughtfully updated, creating a move-in-ready space with a fresh, contemporary feel throughout. Located in a great neighborhood known for its excellent schools, this home is ideal for families seeking comfort, style, and convenience. Don’t miss this rare opportunity to own a fully renovated home in a prime location! Roof 2021 AC 2025 Water heater 2025
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lori Citek (407-616-1692)
2033 TIMBER LN, CLEARWATER, FL 33763
$309,00022 Days on yellowkey MLS ID: TB8505992
0 Days Off yellowkey (back on 5/11/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 980 Built: 1960Monthly Fee: $15 Tax: $893 (2025)Community: GreenbriarSingle Family
Taxes:$893
Remarks: Under contract-accepting backup offers. Welcome to 2033 Timber Lane, a charming 2-bedroom, 2-bath home located in the desirable Greenbriar community. Perfectly situated near US-19, Countryside, Downtown Dunedin, and the Pinellas Trail. HVAC is brand new. Inside, you’ll find a bright and inviting layout featuring a spacious kitchen with abundant cabinet space, classic plantation shutters, and a cozy dining area overlooking the backyard. Added bonus is a generator outlet installed, offering added convenience and peace of mind during storm season. The second bathroom, located in the garage, classic characteristic found in many original Florida homes. Enjoy living year-round from the screened-in patio, the perfect spot for morning coffee and watching the neighborhood peacocks. Greenbriar residents enjoy a low annual HOA fee along with access to community amenities, including a nearby pool, clubhouse, and regular neighborhood events that create a welcoming community atmosphere. This home is full of potential, schedule your private showing today!
Listing is courtesy of: ARC REALTY GROUP (800-636-2080)
Listing Agent: Sapir Simply (727-403-0507)
2047 GREENBRIAR BLVD, CLEARWATER, FL 33763
$299,99930 Days on yellowkey MLS ID: OM723771
0 Days Off yellowkey (back on 5/8/2026)
Bed: 2 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1128 Built: 1961Monthly Fee: $12 Tax: $905 (2025)Community: GreenbriarSingle Family
Taxes:$905
Remarks: Under contract-accepting backup offers. Live the Florida lifestyle you have been looking for in this comfortable 2 bedroom, 1 and 3/4 bathrooms single family home on Greenbriar Blvd in Clearwater. Designed for both everyday charm and easy entertaining, the home features a flexible layout with a bright living room, separate family room, formal dining space, and a casual dining area just off the kitchen. Enjoy seamless indoor outdoor living as you step onto your private wood deck, perfect for morning coffee, relaxed evenings, or hosting friends. A two car garage adds convenience and extra storage. Set within a quiet, established neighborhood, this home offers a peaceful setting while keeping you close to everything Clearwater and nearby Dunedin has to offer, from beautiful Gulf beaches minutes away to local golf courses, shopping, dining, and everyday essentials. For those seeking added amenities, Greenbriar Club is an optional HOA that provides access to a community pool, fitness center, and clubhouse, within walking distance giving you even more ways to enjoy your time at home. Whether you are looking for a full time residence or a seasonal retreat, this property offers comfort, flexibility, and a lifestyle buyers love.
Listing Agent: Lelah Hughes (407-342-2334)
2001 GREENBRIAR BLVD #6, CLEARWATER, FL 33763
$74,900164 Days on yellowkey MLS ID: TB8457115
REDUCED by $3,000 (3.9%) on 05/05/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 605 Built: 1970 Tax: $522 (2024)Community: Greenbriar CondoCondo
Taxes:$522
Remarks: Seller Motivated! and New Price!!! and great value on a ground floor condo to make you winter escape to, for under 80k, this is perfect! Great location, 10 minutes to all the things you need, want and shopping! Dunedin and Safety Harbor are 10 minutes away, also! And Blue Jays Spring training games are a quick 2 miles away and the Phillies are 3 miles!!! One Monthly fee cover water, sewer, trash, cable, internet, exterior maintenance of the building, roof and insurance of the building, you just pay the monthly electric bill. Most of the furniture stays; this gives you a great start on your Florida getaway or full-time home. Heated pool and clubhouse for 140. a year for a single person, all tile flooring throughout, nice sized bedroom with walk in closet. French doors welcome you to Florida or Flex room space. No flood insurance required here, high and dry! This is a 55+ community, no pets, but an emotional need pet could be approved and no leasing in this building. Laundry in building and is free to use! What more could you want! Come check it out!
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Stephanie Hanks (727-735-3374)
2087 HILLWOOD DR, CLEARWATER, FL 33763
$325,000214 Days on yellowkey MLS ID: TB8442158
1 Days Off yellowkey (back on 5/2/2026)
REDUCED by $25,000 (7.1%) on 04/16/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1607 Built: 1972Monthly Fee: $18 Tax: $1,502 (2024)Community: GreenbriarSingle Family
Taxes:$1,502
Remarks: Under contract-accepting backup offers. Short Sale. The shortsale was approved at $325,000 and seller will consider $325,000 offers. NEED A CASH OFFER. HOME NEEDS A ROOF. Not leaking but at the end of it's life. No repairs will be made by the seller. Subject for an updated approval by the lender. How wonderful to be high and dry and still have a view of the lake. This wonderful two-bedroom, two-bathroom home could be yours. Located in the desirable Greenbriar subdivision, Clearwater. Enjoy the Greenbriar community amenities for only $210 per year! As you step through the front door, a spacious living room and dining room area is waiting for you. The kitchen offers light cabinetry, laminate flooring and a corner breakfast nook, a nice bright kitchen. The home also features a large indoor laundry room complete with a utility sink and cabinets for storage. Transition from the kitchen or the dining area to the large family room featuring a beautiful brick woodburning fireplace and a huge picture window with a beautiful view of the lake in the backyard, truly picturesque. In the backyard there is a large patio area overlooking the lake, perfect for relaxing and enjoying the weather and ideal for having a barbeque! Recent updates to the home include newer hot water heater and impact resistant windows in the front and the south side of the house. Centrally located in Pinellas County with easy drives to Clearwater Beach (20 minutes), Downtown Dunedin (10 minutes) St. Petersburg/Clearwater Airport (20) minutes and Tampa International Airport (30 minutes). Do not let this opportunity slip away! Schedule your private tour today and see for yourself why this delightful home is the perfect place to create lasting memories.
Listing is courtesy of: KELLER WILLIAMS REALTY PORTFOLIO COLLECTION (727-489-0800)
Listing Agent: Tammy Mcinerney (727-434-1800)
2536 BRAMBLEWOOD DR W, CLEARWATER, FL 33763
$454,900166 Days on yellowkey MLS ID: TB8456531
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1508 Built: 1973 Tax: $6,886 (2024)Community: GreenbriarSingle Family
Taxes:$6,886
Remarks: Under contract-accepting backup offers. Looking for downtown Dunedin vibes, without the downtown Dunedin living price tag? Well then this fully updated 3 bedroom, 2 bathroom jewel is for you. Especially with its PRICE IMPROVEMENT. Festivals, farmers markets, Honeymoon Island, and the Dunedin Causeway are just minutes away, while you pay less "to play” in the highly sought-after Greenbriar community. Inside you will find freshly painted walls that frame an open concept living room and kitchen which features solid cherry wood cabinets, stainless steel appliances and granite countertops. Both rooms flow seamlessly into an enormous 25’ x 9’ bonus room. One bonus room. Infinite personalities! Playroom, gym, office, family room, craft cave? Your lifestyle, your rules, you choose! A coveted split floor plan offers privacy where it matters, featuring a spacious primary suite with a walk-in closet and a modern, updated bath complete with a large soaker tub/shower combo. On the opposite side of the home, you’ll find two generously sized guest bedrooms with ample closets, perfect for visitors, family, or home office. A designer grade, updated guest bathroom adds a little sparkle and rounds out the guest wing. Recent home glow-ups include- all new plumbing installed in 2024, 3-ton HVAC unit (June 2022), roof (2014), water heater (2024), new well pump (2024), newer windows and updated irrigation system, ensuring that all the big stuff is already done so your to-do-list is a small one. Outside, enjoy a newly sodded front-yard, flanked by native landscaping, and a “Florida” farm-to-table backyard, complete with mango, pomegranate and loquat trees. Your backyard called and it’s bringing the snacks! A new well pump keeps all your greens watered without spending a lot of green, while $35,000 in PAID-OFF solar panels keep your electric bills under $100 per month so you can let the sunshine in without watching your money fly out the window. Greenbriar is a deed-restricted community with an impressively low HOA that offers access to a slew of amenities without that “what am I paying for?” feeling that include a heated community pool, fitness center, clubhouse, library, game room, and shuffleboard courts. If you are looking for a home that will impress with its updated systems, flexible space, unbeatable location, and serious savings, then come see why this Greenbriar gem is an easy yes!
Listing is courtesy of: BLAKE REAL ESTATE INC (727-359-0388)
Listing Agent: Julie Perretta Mccarthy (843-324-0510)
2317 INDIGO DR, CLEARWATER, FL 33763
$290,00065 Days on yellowkey MLS ID: TB8490591
0 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 912 Built: 1960 Tax: $1,204 (2025)Community: GreenbriarSingle Family
Taxes:$1,204
Remarks: Under contract-accepting backup offers. Here is a great chance to get a 2 Bedroom, 2 full bath, block home in Clearwater with a garage. Located in the desirable Greenbriar neighborhood, this home features a tile roof, large back yard with a covered patio and washer and dryer in the garage. Circular driveway, newer central heat and air. A short distance to shopping, Downtown Dunedin, Dunedin Causeway and Honeymoon Island.
Listing is courtesy of: BRICK HOUSE REALTY SERVICES (727-804-4992)
Listing Agent: Joe Courey (727-804-4992)
2549 WYNNEWOOD DR, CLEARWATER, FL 33763
$380,00066 Days on yellowkey MLS ID: TB8490284
2 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1641 Built: 1973Monthly Fee: $18 Tax: $134 (2025)Community: GreenbriarSingle Family
Taxes:$134
Remarks: Under contract-accepting backup offers. Welcome to this spacious 2-bedroom, 2-bathroom home offering 1,641 sq ft of living space, perfectly positioned on a desirable corner lot in a highly sought-after community. Filled with natural light throughout, this home features a versatile layout with endless potential to make it your own. Enjoy year round comfort in the enclosed Florida room, complete with A/C and heat, perfect for a second living space, home office, or relaxation area. Step outside to the additional screened-in back patio, ideal for enjoying Florida evenings without the bugs. With great bones and plenty of space, this home is ready for someone to bring their vision and transform it into something truly special. Located in the desirable Greenbriar community, residents enjoy a deed-restricted neighborhood with a low HOA and access to fantastic amenities, including a heated pool, clubhouse, fitness center, library, game room, and shuffleboard courts. Offering incredible value without the high cost. The location is hard to beat. Just minutes from local festivals, farmers markets, Honeymoon Island, and the Dunedin Causeway. You’re also a short drive to the beautiful Gulf beaches, vibrant downtown Dunedin with its marina, shops, and dining, and convenient access to Westfield shopping. Tampa International Airport is approximately 30 minutes away, making travel a breeze. This is an incredible opportunity to own in one of the area’s most desirable communities. Schedule your showing today, don’t miss your chance to make it yours.
Listing is courtesy of: RE/MAX REALTY UNLIMITED (813-684-0016)
Listing Agent: Kaley Clopton (407-508-0860)
2371 INDIGO DR, CLEARWATER, FL 33763
$314,90072 Days on yellowkey MLS ID: TB8487837
2 Days Off yellowkey (back on 4/22/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1070 Built: 1962 Tax: $5,055 (2025)Community: GreenbriarSingle Family
Taxes:$5,055
Remarks: Under contract-accepting backup offers. Waterfront living without the worry, this well maintained 2 bedroom, 2 bathroom home with a 1 car garage is ideally located in Greenbriar and NOT in a flood zone. The home is also equipped with solar panels, offering added energy efficiency and long term savings. Offering a relaxed coastal feel in the heart of Clearwater near Dunedin, this home blends comfort, functionality, and scenic views. Inside, the kitchen is finished with quartz Cambria countertops and flows easily into the main living areas, creating a layout that works for both everyday living and entertaining. The spacious primary suite features a private bathroom and a walk-in closet. The sun drenched Florida room adds additional living space, perfect for relaxing or enjoying the peaceful surroundings. Step outside to a low maintenance front yard and a beautifully scenic backyard with lush green grass and tranquil water views that feed into nearby Jerry Lake, offering opportunities for fishing and outdoor enjoyment right from your own backyard. Greenbriar residents enjoy access to a heated community pool, fitness room, and an active clubhouse with regular events and activities, all while maintaining a low HOA. The location truly stands out, just minutes from Countryside Mall for shopping and dining, and a short drive to the restaurants, breweries, and waterfront parks of Downtown Dunedin and Downtown Clearwater. You are also conveniently close to the Pinellas Trail, multiple golf courses, local hospitals, and spring training stadiums for both the Philadelphia Phillies and Toronto Blue Jays. Best of all, the world famous Clearwater Beach is approximately 8 miles away, making it easy to enjoy white sand beaches and stunning Gulf sunsets whenever you choose. Schedule your showing today.
Listing Agent: Calvin Pringles (727-244-7854)
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