Location: Clearwater , 33761
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2894 ROLLINGWOOD CT, CLEARWATER, FL 33761
$880,00088 Days on yellowkey MLS ID: TB8465056
0 Days Off yellowkey (back on 4/1/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2411 Built: 1981 Tax: $9,835 (2024)Community: Countryside Tr 55Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,835
Elementary School: Curlew Creek Elementary-PN
High School: Countryside High-PN
Tax Year: 2024
Middle School: Safety Harbor Middle-PN
Remarks: Under contract-accepting backup offers. Prepare to be impressed by this fully remodeled Clearwater gem, ideally located off Rollingwood and Landmark Drive. From the moment you arrive, the curb appeal and prime corner-lot setting set the tone. Situated on a fenced ¼-acre cul-de-sac lot, this home offers space, privacy, and a location that immediately excites buyers. The updated French entry doors welcome you into a home that truly opens up. Inside, expansive ceilings and a wide-open layout create an immediate sense of light and flow. The oversized dining room makes a statement, complemented by knockdown texture throughout and energy-efficient LED lighting that enhances the modern design. The kitchen anchors the home, seamlessly connecting to the living area-perfect for entertaining and everyday living. Featuring all-new two-tone cabinetry with abundant pull-out drawers, this space is designed to satisfy the home chef. Quartz countertops, stainless steel appliances, and a sleek contemporary backsplash complete the look. The living room is elevated by a custom built-in entertainment center with an electric fireplace and dedicated space for home entertainment. The primary suite offers tranquil poolside views and a stunning, fully updated en-suite bathroom with a glass-enclosed shower and tub. Dual vanities with modern finishes and lighted mirrors bring both style and function. Just off the primary suite, the fourth bedroom provides incredible flexibility ideal for a home office, nursery, sitting room, or additional bedroom. A true split floor plan places two additional bedrooms on the opposite side of the home, along with a beautifully updated hall bath featuring contemporary charm. Impact-rated windows enhance energy efficiency while improving storm readiness and peace of mind. Major systems have been updated in 2025 and 2026, including the main electrical panel, HVAC water heater, roof, pool pump and windows, offering buyers confidence and long-term value. Step into the backyard and see where this home truly shines. The oversized pool has just been refinished with a durable Diamond Brite surface for years of low-maintenance enjoyment. The pool deck and entry walkway feature contemporary stamped concrete, flowing seamlessly to the covered back patio. Rain or shine, outdoor living continues with an expansive covered entertaining space just off the kitchen, complete with an outdoor refrigerator to keep gatherings effortless. The large two-car garage easily accommodates vehicles and even fits a golf cart (sold separately). This is a rare opportunity to own a turnkey, fully remodeled home with space, style, and a backyard built for Florida living, all in a desirable Clearwater location. Immediate Appointments Available!!
Listing is courtesy of: REALTY EXPERTS (727-888-1000)
Listing Agent: Shannon Ibrahim (727-228-2001)
27466 US HIGHWAY 19 N #77, CLEARWATER, FL 33761
$85,90087 Days on yellowkey MLS ID: TB8466742
REDUCED by $3,600 (4.0%) on 04/01/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1970Monthly Fee: $110 Tax: $526 (2024)Community: Countryside Estates Mobile Home Park UnrecMobile Home
Taxes:$526
Elementary School: None
High School: None
Middle School: None
Remarks: Located in a desirable 55+ community in Clearwater, Florida, this property offers ownership of your share of the land with no lot rent. The beautifully remodeled 12’ x 60’ home features a 16’ x 22’ side addition, providing a spacious and comfortable layout with 2 bedrooms and 1 bathroom. The home is turn-key and move-in ready. Ideally situated just 15 minutes from Clearwater Beach and 5 minutes from Dunedin Beach. Walk to grocery stores and to Countryside shopping mall Baseball fans will appreciate being only 10 minutes from Toronto Blue Jays and Philadelphia Phillies spring training facilities. The low association fee of $110 monthly includes lawn care, garbage, and water. Annual property taxes are approximately $600. This is a wonderful opportunity for affordable living in a well-maintained community—perfect for seasonal or year-round residence. Enjoy the Florida lifestyle and sunshine all year long. MUST OWN FOR 2 YEARS PRIOR TO RENTING..
Listing is courtesy of: AMERICAN HERITAGE REALTY, INC. (727-726-7272)
Listing Agent: Michael Peters (727-251-0531)
3021 COUNTRYSIDE BLVD #24A, CLEARWATER, FL 33761
$299,000385 Days on yellowkey MLS ID: TB8366035
3 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1820 Built: 1975 Tax: $1,602 (2025)Community: Brynnwood Condo 1Condo
Taxes:$1,602
Tax Year: 2025
Remarks: Under contract-accepting backup offers. $26,000 PRICE REDUCTION!!! PLEASE CALL ME FOR A PRIVATE SHOWING! Welcome to this gorgeous 3 Bedroom, 2 Bath, 1820 sq feet Condo located in the desirable 55 plus community of "Brynnwood"! Step inside this Light and Bright south facing unit. This condo offers all IMPACT RATED PGT HURRICAINE WINDOWS & SLIDERS, is NOT IN A FLOOD ZONE & is centrally located within the Countryside area. Additional features of this condo are large spacious bedrooms, plantation shutters on all windows, Newer cream shaker style kitchen cabinets with granite countertops, and lots of natural light throughout! This well-maintained community is surrounded by serene fountains, amazing tropical landscaping and a sparkling heated Pool! Each unit comes with an under building parking space and storage closet and on each floor is a community storage closet and rubbish closet. There is plenty of additional parking outside each building for your family and guests to visit. Brynnwood is located in a prime spot with Countryside Country Club next door that offers Golf, Tennis Courts, fitness center, Swimming Pools and a clubhouse with a Restaurant. Many different memberships are available there. Also close by is the Countryside Mall, Hospital, Downtown Safety Harbor, Downtown Dunedin, Performing Arts Center, and Beaches! Come and enjoy the peace and serenity of this gorgeous home.
Listing is courtesy of: LOWE AND SONS INC. (727-799-2894)
Listing Agent: Joyce Lowe (727-799-2894)
2500 WINDING CREEK BLVD #I104, CLEARWATER, FL 33761
$248,00017 Days on yellowkey MLS ID: TB8492314
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 946 Built: 1987 Tax: $2,088 (2025)Community: Fountains At Countryside CondoCondo
Taxes:$2,088
Remarks: Experience elevated Florida living in this completely reimagined, first-floor 2-bedroom, 2-bath, easily functioning as two private primary suites in the gated community of The Fountains at Countryside. This is not a simple update but rather a full-scale renovation where virtually every surface and detail has been replaced, delivering a truly like-new living experience. The kitchen has been beautifully transformed into a standout feature of the home, offering upgraded appliances, sleek countertops, and a functional layout enhanced by a window overlooking the tranquil courtyard fountain, bringing in natural light and a peaceful view rarely found. It’s a space that blends everyday practicality with clean, modern design. The expansive living area opens through sliding glass doors to a screened lanai with serene views of the resort-style pool, creating a seamless indoor-outdoor living experience. Additional highlights include a private indoor laundry closet with stackable washer and dryer, a new A/C system installed in 2025, a semi private fountain courtyard, and a covered carport. Throughout the home, you’ll find a cohesive, high-quality finish level that elevates every room, creating a polished yet comfortable environment that immediately stands apart from typical condo offerings. Residents of The Fountains at Countryside enjoy a maintenance-free lifestyle with an impressive array of amenities, including a heated pool and spa, elegant clubhouse, state-of-the-art fitness center and yoga studio, dog park, butterfly garden, grilling stations, and beautifully landscaped walking paths. Monthly HOA fees cover security, exterior maintenance, water, sewer, trash, cable TV, pest control, and more, delivering both value and convenience. Perfectly positioned near top-rated beaches, shopping, dining, and major thoroughfares, this home offers the ideal blend of tranquility and accessibility. This is more than a condo-it’s a turnkey, resort-style retreat where every day feels like a vacation.
Listing is courtesy of: PREFERRED SHORE REAL ESTATE (941-999-1179)
Listing Agent: Derek Golden Llc (727-240-6255)
3034 EASTLAND BLVD #D104, CLEARWATER, FL 33761
$179,90043 Days on yellowkey MLS ID: TB8482206
REDUCED by $10,000 (5.3%) on 03/31/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 750 Built: 1980 Tax: $1,806 (2025)Community: Imperial Oaks CondoCondo
Taxes:$1,806
Elementary School: Leila G Davis Elementary-PN
Remarks: One or more photo(s) has been virtually staged. Welcome home to an exceptional opportunity in the highly desirable Imperial Oaks Condo Association — a residence where style, comfort, and thoughtful upgrades blend seamlessly into one beautiful space. Completely remodeled in 2024 and enhanced with over $36,000 in updates and improvements, this stunning one-bedroom, one-bathroom condo is truly move-in ready. From the moment you step inside, you’ll be captivated by the elegant vinyl plank flooring that flows effortlessly throughout, creating a warm and modern aesthetic. Natural light pours in, while hurricane impact windows at the rear of the unit provide both peace of mind and energy efficiency. The kitchen is a showstopper — featuring sleek quartz countertops, a striking tile backsplash, all-new stainless steel appliances, and a deep commercial-grade sink designed for both beauty and function. Every detail has been carefully curated, from the new fixtures and outlets to the four-stage reverse osmosis water filtration system, ensuring pure comfort in everyday living. Retreat to a serene bedroom enhanced by custom-made doors, while the fully updated bathroom impresses with a stylish new vanity and coordinating tile backsplash. Practical upgrades such as a new hot water heater, new washer and dryer, and new front and rear screen doors add convenience and value to this meticulously maintained home. Ideally situated near the community pool, this charming condo also offers exceptional walkability — just a short distance to two vibrant plazas with supermarkets, popular eateries, Starbucks, Bonefish Grill, and so much more. Whether you’re enjoying a quiet evening at home or exploring the nearby conveniences, this residence delivers the perfect blend of tranquility and accessibility. All that’s left to do is move in and start living beautifully.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Vanessa Leonard (727-647-2706)
2400 WINDING CREEK BLVD #24-102, CLEARWATER, FL 33761
$159,900351 Days on yellowkey MLS ID: TB8381056
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 998 Built: 1975 Tax: $2,473 (2025)Community: Winding CreekCondo
Taxes:$2,473
Remarks: Charming renovated first floor unit in the heart of the Clearwater-Countryside area that is an ideal location to be close to everything including restaurants, shopping, theaters, hospitals and beach community. This furnished condo is move-in ready! Loads of updates include a BRAND NEW ROOF - 2025, HVAC SYSTEM 2022, NEW LANAI WINDOWS 2024, WATER HEATER, NEW FLOORING and is completely furnished. The condo offers the ideal combination of comfort, convenience and is located only 5 miles to the gorgeous Honeymoon Island State Park Beach. This condo residence radiates a renewed sense of vibrancy that you'll love coming home to with heated pool, hot tub and more. This unit is a cozy split floor plan with a modern renovated bathroom. The Kitchen has plenty of cabinets and countertops with a welcoming ambiance that perfectly compliments the dining area and living room space. There is a in-unit laundry with washer and dryer included. Adjacent to the living area is the fully enclosed lanai area with new hurricane windows with tile flooring and views of the courtyard and beautiful landscaping. This community is located in a non-evacuation zone, no flood zone and does not require structural or milestone inspections. The HOA fee includes water, sewer, trash, basic cable and internet, maintenance and insurance that includes the roof, covered parking and landscaping. Winding Creek offers a heated swimming pool and hot tub to relax in after a long day. There is a covered patio area for eating and relaxing and a clubhouse with kitchen area and recreation room. There is a tennis court and/or pickleball court, shuffleboard and bar-b-que area for grilling. If you want to have a party to entertain your friends and family the clubhouse is available for rental. There are so many amenities available for your Florida dream home. Whether you're seeking a primary residence, a vacation getaway, or an investment opportunity, this property checks all the boxes. Don't miss out on the chance to make it your own and enjoy the benefits of homeownership. Contact me today to schedule a viewing and turn your dreams into reality.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Sharon Vecchione (727-781-3700)
3443 BARONNE CT, CLEARWATER, FL 33761
$219,90042 Days on yellowkey MLS ID: TB8483971
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1980Monthly Fee: $544 Tax: $4,891 (2025)Community: Chateaux Woods CondoVilla
Taxes:$4,891
Remarks: Clearwater 2-bedroom, 2-bath villa with a 1-car garage and a new roof being installed by the HOA in the desirable Chateaux Woods community. This single-story home features a spacious living and dining area that flows into a bright enclosed Florida room, offering flexible space for a den, office, or additional living area. The primary suite includes a walk-in closet and private bath, while the second bedroom provides comfortable space for guests or a home office. Residents of Chateaux Woods enjoy a peaceful, well-maintained community with mature landscaping and a community pool. The monthly condo fee covers exterior maintenance, lawn care, roof, cable TV, and internet for easy, low-maintenance living. Conveniently located near shopping, dining, parks, the Pinellas Trail, medical facilities, Tampa International Airport, St. Pete–Clearwater International Airport, and the Gulf beaches, this villa offers excellent value in a central Clearwater location.
Listing Agent: Arthur Panagopoulos (727-744-2205)
2587 COUNTRYSIDE BLVD #6107, CLEARWATER, FL 33761
$169,000175 Days on yellowkey MLS ID: TB8441455
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 955 Built: 1982 Tax: $2,939 (2024)Community: Inverness CondoCondo
Taxes:$2,939
Remarks: LOW HOA FEE & NO FLOOD INSURANCE REQUIRED!! SELLER IS MOTIVATED!! Move-in ready, fully furnished 2-bedroom, 2-bath first-floor condo in Inverness at Countryside. This beautifully updated Countryside condo features ceramic tile flooring throughout and a modern galley kitchen with stainless steel appliances and a convenient pass-through to the open dining and living area. The spacious primary suite includes a private balcony, walk-in closet, and an updated en-suite bath with a walk-in shower. A split-bedroom layout offers privacy for guests, with a large second bedroom and full bath with tub/shower combo. In-unit washer and dryer are included for everyday convenience. The building has completed inspections with no current assessments, offering peace of mind. Ideally located across from Westfield Countryside Mall, residents enjoy easy access to Clearwater shopping, dining, entertainment, and Gulf Coast beaches. This turnkey 55+ Clearwater condo is beautifully maintained and ready for immediate occupancy — ideal as a primary residence or seasonal Florida retreat.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
2563 KNOTTY PINE WAY, CLEARWATER, FL 33761
$899,00058 Days on yellowkey MLS ID: TB8477008
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3172 Built: 1978Monthly Fee: $3 Tax: $10,071 (2025)Community: Northwood Estates - Tr FSingle Family
Taxes:$10,071
Remarks: Located in the highly desirable Countryside Northwood Estates, this spectacular 4-bedroom, 3-bath residence with a versatile bonus room offers the perfect blend of elegance, comfort, and resort-style living. A grand foyer with a rounded archway welcomes you into expansive formal living and dining areas, ideal for entertaining. The beautifully renovated 2023 kitchen showcases stunning quartzite waterfall countertops, new appliances, and an open-concept design overlooking the main living spaces. Gleaming hardwood floors, a sweeping staircase, soaring ceilings, and crown molding enhance the home’s timeless appeal. The first floor features a private fourth bedroom and office, while the spacious family room centers around a charming brick wood-burning fireplace. Upstairs, the enormous primary suite boasts dual closets, private bathroom with dual vanities and a newly renovated shower, and French doors leading to a private balcony overlooking your backyard paradise. This home’s rare Florida basement—with interior access and new sump pumps (2024)—offers endless possibilities for storage, hobbies, or future expansion. Step outside to a true entertainment showplace: a tropical oasis complete with a sparkling in-ground pool (new pump 2021), covered outdoor living space, bar area, tiki hut, natural gas grill, stone fire pit, white sugar-sand accents, new vinyl fencing with dual gates, and an outdoor shower with pool bath access and jacuzzi spa tub. Major upgrades provide peace of mind and efficiency, including solar panels (2022), a two-floor HVAC system (2021), dimensional shingle roof (2020), tankless gas water heater, private well irrigation, fresh interior and exterior paint, updated bathrooms, and a new garage door system (2025). High and dry with no flood insurance required, this exceptional property also offers convenient access to the world-famous beaches, Safety Harbor, Dunedin, Tampa, and St. Petersburg. Schedule your private showing today and experience the ultimate staycation lifestyle at home.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
3031 COUNTRYSIDE BLVD #35C, CLEARWATER, FL 33761
$325,00061 Days on yellowkey MLS ID: TB8476247
0 Days Off yellowkey (back on 2/22/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1820 Built: 1975 Tax: $5,366 (2025)Community: Brynnwood Condo 1Condo
Taxes:$5,366
Remarks: Under contract-accepting backup offers. Fabolous Florida Condo in the heart of Countryside! The Community sits adjacent to Countryside Country club along hole #1 on professional Countryside Golf course. Additional community amenities include New Roof , assigned, under-building parking space & storage, ample guest parking, lush- tropical landscaping with mature palm trees and native Florida plants nestled along a courtyard walkway leading to relaxing pool. Additionally, there are 2 elevators to comfortably bring you to the third-floor double door entry to your new home. Inside you’ll discover the kitchen opens to a dining/breakfast area near the open oversized living room with wet bar and a gorgeous view through the sliding glass doors that open to the expansive wrap around balcony to sit and enjoy the outdoors. Features include a private laundry room with utility sink & full-sized washer & dryer. Down the hall there are 2 bedrooms adjacent to a main bathroom great for an office or guests. The primary bedroom suite has a large walk-in closet, double sink vanity & shower. Updates include: A/C 2023 /Water heater 2024/ Frige 2024/Dishwasher 2023/New sink & Disposal 2024/Granite Bathroom Counters 2024/ Dryer included(new 2024) . Brynnwood is a 55+ community. The Countryside Country Club offers golf, tennis, fitness center, and social memberships and is right next door! The Countryside Library and Countryside Recreation Center are just down the street, while the Countryside Mall, offers shopping, restaurants and movie theaters as additional plus. Located near Top rated Beaches, downtown Safety Harbor & Dunedin! Easy commute to Tampa, St. Pete, Tampa or Clearwater/ St Pete International Airport, Tampa Cruise Port and many professional golf courses.
Listing is courtesy of: CENTURY 21 COAST TO COAST (727-726-4757)
Listing Agent: Jennifer Whitaker (727-458-7042)
2650 COUNTRYSIDE BLVD #F209, CLEARWATER, FL 33761
$194,90098 Days on yellowkey MLS ID: TB8462207
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1110 Built: 1978 Tax: $1,886 (2024)Community: Rustlewood At Countryside CondoCondo
Taxes:$1,886
Remarks: Centrally located in beautiful and quiet Rustlewood Condos in the heart of Countryside! Walk to Countryside mall, minutes to top rated beaches, quaint Downtown Safety Harbor, charming Downtown Dunedin, top rated golf courses, The Pinellas Trail, shopping, dining, top notch medical facilities, and a 25 minute drive to the Tampa International Airport! This 2 bedroom/2 bathroom condo features an open and airy living space with great natural light and two spacious bedrooms. The kitchen has been completely remodeled along with the flooring throughout. The primary bedroom has a walk-in closet, updated ensuite bathroom, and sliding glass doors that lead out to the screened in balcony/porch. The second bedroom and closet are a nice size and have access to the hallway bathroom. Laundry facilities are located inside the unit in a hallway closet. HVAC 2023/ Updated Electric Panel 2022/ NON-FLOOD ZONE Enjoy the beautifully landscaped common grounds, pond, and community pool! Each unit includes an assigned parking space and there is plenty of guest parking. Monthly fee includes escrow reserve funds, building insurance, community pool, building maintenance, grounds maintenance, sewer, trash, and water. Come and make this move-in ready condo yours today!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Elena Kapetaneas (727-515-9693)
2568 W BROOK LN, CLEARWATER, FL 33761
$299,900395 Days on yellowkey MLS ID: W7873616
1 Days Off yellowkey (back on 3/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1253 Built: 1993Monthly Fee: $325 Tax: $1,191 (2024)Community: BrookfieldVilla
Taxes:$1,191
Middle School: Palm Harbor Middle-PN
Remarks: Under contract-accepting backup offers. Welcome to this beautiful, freshly custom painted 2-Bedroom, 2-Bathroom, 1-Car Garage villa located within the Brookfield subdivision in Clearwater. Your newly roofed home includes an updated kitchen, with new appliances, soft-closed cabinetry, along with a new skylight for natural light! New luxury vinyl tile along with ceramic tile floors have been installed throughout the home, bathroom updates, and all new ceiling fans. The interior windows have all been decoratively enhanced with the installation of new plantation shutters. Also, the sliding glass door leading to the enclosed lanai and the master bed door leading out to the patio includes new blackout roller shades. The lanai leads to an enclosed, newly landscaped backyard where you have the luxury of relaxation. Community amenities include a clubhouse, lighted tennis/pickleball courts, two pools and spas (one is heated in the winter), and two beautiful ponds. The low monthly fee covers building exterior painting, front yard ground maintenance, community pools, roof, trash removal, and fence repairs. A short drive to beaches, Countryside Mall, downtown Safety Harbor, Dunedin, and Honeymoon Island.
Listing is courtesy of: ISLAND REAL EST&PROP MGMT INC (727-804-7719)
Listing Agent: Anthony Fig Figliomeni (716-622-0752)
29250 US HIGHWAY 19 N #141, CLEARWATER, FL 33761
$159,000161 Days on yellowkey MLS ID: TB8445322
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1974Monthly Fee: $238 Tax: $1,552 (2024)Community: Doral Ro Association Inc UnrecMobile Home
Taxes:$1,552
Remarks: SUBSTANTIAL PRICE REDUCTION! Discover a truly uplifting lifestyle in this exceptional 2-bedroom, 2-bathroom home, displaying 1,248 square feet of living space set in the amenable Doral Village, a gated 55+ community in beautiful Clearwater, FL. With a budget-friendly maintenance fee of just $238.00, residents enjoy the simplicity of having water, sewer, garbage, and lawn care included, allowing free time for enriching amenities. The neighborhood radiates warmth and camaraderie, even for your feline companions ( 2 cats permitted in the park), offering enjoyable activities such as billiards and shuffleboard, as well as relaxation in a heated pool and spa, all designed to enhance social engagement. Perfectly situated just a hop, skip, and a jump from sparkling beaches, convenient supermarkets, fantastic restaurants, and close proximity to airports. This ideally located home offers a wonderful blend of indoor comfort and outdoor enjoyment. INTERIOR: Open the door to this welcoming, expansive home, where every detail invites comfort, elegance, and everyday livability. The rare floor plan offers an open flow, highlighted by a beautifully updated kitchen featuring a breakfast bar, modern appliances—including a fridge, range oven, dishwasher, ice maker, and microwave—and appealing laminate flooring throughout most of the home. Tasteful paneling, updated windows, central heat and air, and ceiling fans ensure both visual appeal and climate-controlled comfort all year. Fully furnished with elegant accessories, the splendid dining room is ideal for hosting memorable family gatherings, while the attractive living room sets the scene for lively movie or game nights. Guests will appreciate the pleasant guest bedroom, adorned with beautiful furnishings, textured ceilings, and mirrored closets, while the inviting guest bathroom features a tiled walk-in shower, new vinyl plank flooring and a sleek vessel sink. The spectacular primary bedroom feels like a resort retreat, boasting French doors that open to an impressive Florida room with ample seating for morning coffee or tea and is air conditioned for added comfort. Mirrored closets, a magnificent bath with double vanities, and a shower and tub combination complete the luxurious atmosphere. Please read on, there’s even more to discover on the exterior of this remarkable home! EXTERIOR: The exterior of this breathtaking home is just as inviting as the interior, featuring low-maintenance vinyl siding that enhances both beauty and durability. A cozy sitting area nestled within the spacious carport offers the perfect spot to relax and enjoy the neighborhood ambiance, while the carport itself easily accommodates two vehicles for ultimate accessibility. French doors open directly from the front porch of the home, welcoming you inside or connecting seamlessly to outdoor living. Awnings on the home increase the curb appeal, already adorned with tasteful landscaping. The shared shed houses a washer and dryer, plus extra storage space, with a passage that leads back to the Florida room. Priced at just $159,000 with a share included, this remarkable property offers exceptional value for those seeking a phenomenal home in an outstanding community. Call today to schedule your private showing!
Listing is courtesy of: SELECT REAL ESTATE OF PINELLAS (727-584-3588)
Listing Agent: Patricia Long (727-584-3588)
2741 FOXFIRE CT #D, CLEARWATER, FL 33761
$279,90057 Days on yellowkey MLS ID: TB8474335
0 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1785 Built: 1974 Tax: $1,427 (2025)Community: Winding Wood CondoCondo
Taxes:$1,427
Remarks: Under contract-accepting backup offers. FULLY RENOVATED 4BR townhome with nearly 1,800 sq ft and ALL NEW major systems including NEW AC, NEW water heater, NEW electrical panel, UPDATED plumbing, and ALL NEW appliances. NEVER LIVED IN SINCE RENOVATIONS and completely move-in ready. One of the LARGEST floorplans in Winding Wood and rarely available. Located on a quiet cul-de-sac in Clearwater’s highly desirable Countryside area and surrounded by expansive open green space, offering uncommon privacy and openness within the community. The main living area features a dramatic 20-FOOT VAULTED CEILING creating a bright and spacious feel. The first floor includes a large bedroom with a full bathroom nearby, ideal for guests, office use, or flexible living. The kitchen features custom maple cabinetry and solid one-inch granite countertops. Sliding glass doors open to an exceptionally large private outdoor patio enclosed by six-foot walls, providing rare privacy and ample space for outdoor seating, entertaining, or gardening, with tile flooring creating a seamless indoor-outdoor connection. Upstairs includes a spacious primary bedroom with sliding glass doors, a full bathroom, and two additional bedrooms. All closets, including the walk-in, feature built-in wood shelving. Additional storage is available under the stairs and within the semi-enclosed covered parking structure. COMMUNITY POOL IS A SHORT WALK from the unit, unlike much of Winding Wood where access requires a longer walk or driving. Countryside offers immediate access to dining, shopping, mall, grocery stores, parks, and recreation while remaining set back from heavy traffic in an established residential area. Tree-lined sidewalks extend nearly a mile, the Pinellas Trail runs alongside the community, and Clearwater Beach is approximately 20 minutes away. FULLY UPDATED, MOVE-IN READY, AND COMPETITIVELY PRICED—ONE OF THE BEST VALUE OPPORTUNITIES IN WINDING WOOD.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Gavin Magrath (727-504-2488)
2659 DIAMOND HEAD DR N, CLEARWATER, FL 33761
$600,000112 Days on yellowkey MLS ID: TB8458950
4 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2442 Built: 1977 Tax: $3,374 (2024)Community: Northwood Estates-Tr CSingle Family
Taxes:$3,374
Remarks: Under contract-accepting backup offers. Welcome to 2659 Diamond Head Drive North in Clearwater — a spacious 4-bedroom, 3.5-bath pool home located in Flood Zone X, offering flexible living spaces and a highly convenient Pinellas County location. This two-story residence features formal living and dining rooms, an updated kitchen, and multiple gathering areas designed to support a variety of lifestyles, including work-from-home, multi-generational living, or entertaining. An oversized bonus room (not included in the square footage) provides ideal space for a media room, playroom, home office, or creative studio. Enjoy Florida living with a screened porch and private pool, while the second-floor primary suite offers added privacy from additional bedrooms. The oversized garage provides abundant storage, with laundry currently located in the garage and existing infrastructure in place to relocate it indoors if desired. The home offers a solid foundation with opportunity for personalization. Ideally situated just minutes from Downtown Safety Harbor, waterfront dining, Gulf beaches, Tampa International Airport, shopping, and major roadways and conveniently located near several local sports complexes and athletic facilities, making it well positioned for year-round training, tournaments, and recreational activities. The property is also very close to Mease Countryside Hospital and nearby medical and business centers, adding everyday convenience for healthcare professionals and commuters alike. Zoned for Leila G. Davis Elementary (~0.2 miles), Safety Harbor Middle (~2.0 miles), and Countryside High School (~0.4 miles with iSTEM program), and located near Palm Harbor University High School magnet program. A rare Clearwater opportunity combining space, pool living, Flood Zone X peace of mind, and exceptional access to everything Tampa Bay has to offer.
Listing is courtesy of: TAMPA HOMESTYLES (813-444-5885)
Listing Agent: Jaime Brown (813-444-5885)
2400 WINDING CREEK BLVD #20A, CLEARWATER, FL 33761
$189,90024 Days on yellowkey MLS ID: TB8488692
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1045 Built: 1987 Tax: $2,273 (2025)Community: Winding CreekCondo
Taxes:$2,273
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in the Winding Creek community in Clearwater. This 2-bedroom, 2-bath ground-floor condo offers comfort, style, and convenience—no stairs, just simple, relaxed living. Inside, the kitchen stands out with granite countertops, stainless steel appliances, and a counter bar that opens to the main living space—great for casual meals or gathering with friends. The living and dining areas feel open and connected, finished with luxury flooring that carries throughout the main spaces. The primary suite includes an enlarged bathroom with a beautifully updated vanity, new fixtures, and tile. The second bathroom has been updated with the same level of detail, creating a clean, cohesive feel throughout the home. You’ll also find updated windows that bring in natural light, along with a stackable washer and dryer for everyday convenience. The unit is being sold furnished, making move-in easy. Step outside to your back patio, just a few steps from the community pool—an ideal spot to start your morning or wind down in the evening. Winding Creek offers a peaceful setting with amenities to enjoy, all in a central location. You will be minutes from downtown Dunedin and Palm harbor, and a short drive to the Gulf beaches including Clearwater Beach and Honeymoon Island State Park. Dining, shopping, and outdoor activities are all nearby.
Listing is courtesy of: LIPPLY REAL ESTATE (727-314-1000)
Listing Agent: Len Lipply (727-642-0255)
2978 BROOKFIELD LN, CLEARWATER, FL 33761
$415,00084 Days on yellowkey MLS ID: TB8467896
1 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1780 Built: 1997Monthly Fee: $325 Tax: $2,254 (2024)Community: BrookfieldVilla
Taxes:$2,254
Remarks: Under contract-accepting backup offers. Welcome to this well-maintained villa in the desirable Brookfield at Estancia community. Offering 1780 square feet, this home features an open layout with vaulted ceilings and a split floor plan providing privacy between the primary suite and secondary bedrooms. Recent updates include a new roof and skylights (April 2025), hurricane-rated windows and sliding glass door, garbage disposal (2025), and washer and dryer (2021). The home also features a screened lanai overlooking a beautifully landscaped backyard including landscape lighting, ideal for relaxing or entertaining. The low monthly HOA of $325 includes access to two community pools (one heated), tennis and pickleball courts, clubhouse, trash service, roof replacements, fencing, and ground maintenance. Conveniently located near shopping, dining, Clearwater beaches and Honeymoon Island.Tthis property offers a comfortable and low-maintenance lifestyle in a sought-after community. Call today to scheduled a private showing.
Listing is courtesy of: LISA HALL REALTY, INC (727-742-5830)
Listing Agent: Lisa Hall (727-742-5830)
2593 COUNTRYSIDE BLVD #7313, CLEARWATER, FL 33761
$180,00048 Days on yellowkey MLS ID: TB8480315
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1530 Built: 1984Community: Inverness CondoCondo
Taxes:
Tax Year:
Remarks: PRICE REDUCED - MILESTONE COMPLETED & PASSED with NO ASSESSMENTS for Building 7, offering immediate confidence and long-term value. Welcome to Inverness at Countryside, a well-maintained 55+ community in the heart of Clearwater. This spacious 3-bedroom, 2-bath condo offers over 1,500 sq ft with a functional split-bedroom layout and abundant natural light. The open living and dining areas create a comfortable flow for everyday living or entertaining. The kitchen features an eat-in space and ample cabinetry. The primary suite includes a walk-in closet and private en-suite bath. Enjoy two screened balconies with sliding door access from both the living room and bedrooms, providing additional usable living space year-round. Community amenities include a centrally located pool, tennis courts, and a fully equipped clubhouse. Assigned covered parking and guest parking are included. Monthly fees cover cable, internet, water, sewer, trash, exterior maintenance, reserves, and pest control. Located minutes from Countryside Mall, restaurants, grocery stores, fitness centers, and the Duke Energy Trail, with easy access to Clearwater Beach and surrounding areas. NON-EVACUATION ZONE at one of the highest elevations in Pinellas County. 55+ building.
Listing Agent: Jon Bauer (727-215-0061)
3225 MASTERS DR, CLEARWATER, FL 33761
$649,90031 Days on yellowkey MLS ID: TB8487159
2 Days Off yellowkey (back on 3/22/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2238 Built: 1980Community: Countryside Tr 56 Unit 1Single Family
Remarks: Under contract-accepting backup offers. Welcome to your dream home at 3225 Masters Drive in the beautiful Countryside area of Clearwater, Florida—a beautifully maintained gem in a sought-after golf community! This stunning 3-bedroom, 3-bathroom residence (approximately 2,238 sq ft) boasts an incredible split-plan layout and is in exceptional condition, with major recent upgrades that provide peace of mind and modern comfort. Highlights include: Brand-new roof (2025) for years of worry-free protection Impact sliders and impact windows throughout offering hurricane protection and breathtaking views of the lush backyard and sparkling pool Gorgeous kitchen featuring real wood cabinets, Corian countertops, a fantastic hosting bar, and a convenient service window—perfect for entertaining! The home was once a 4 bedroom but A wall was removed to make one extra large bedroom. You could easily add the wall back to make this a four bedroom if you desired! Large screened-in pool with a child-proof fence for safe family fun Spacious fenced backyard with plenty of room for play, gardening, or future enhancements New water softener (2023), new water heater (2025), and brand-new large gutters (2023) for added efficiency and curb appeal Cozy family room with a real wood-burning fireplace Open great room overlooking the pool for seamless indoor-outdoor living Elegant formal dining room adjacent to the grand, private entrance Enjoy the Florida lifestyle at its finest—close to pristine beaches, major airports, top-rated schools, shopping, dining, and the renowned Countryside Country Club with its Gary Player-designed golf courses. Best of all, this home is not in a flood zone! Priced to sell quickly and move-in ready, this rare opportunity in one of Clearwater's most desirable neighborhoods won't last long. Schedule your private showing today and experience the charm, updates, and unbeatable location for yourself!
Listing is courtesy of: YOU FIRST REALTY AND ASSOC LLC (813-458-6686)
Listing Agent: George Guarino (813-787-0531)
3021 COUNTRYSIDE BLVD #26A, CLEARWATER, FL 33761
$275,000182 Days on yellowkey MLS ID: TB8439039
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1820 Built: 1975Community: Brynnwood Condo 1Condo
Remarks: One or more photo(s) has been virtually staged. MOTIVATED SELLERS. Price Reduction, offering buyer credit with the right offer. Use for temp rate buydown, closing costs or save your cash for renovations. And an appliance warranty! Quiet and rare to find a three-bedroom, two-bath oversized condo with beautiful views of Countryside Golf & Country Club. Located in a non-flood, non-evacuation zone, this well-established 55+ community is truly a hidden gem. This well-cared-for condo offers over 1,800 square feet of comfortable living space. You have a reserved under-building parking space and the convenience of two elevators that bring you directly to your second-floor home. The southern exposure fills the unit with natural light without direct sun. Enter through double front doors into a welcoming foyer. The spacious layout features a wet bar, a large living and dining area with plush carpeting installed in 2023, and sliding doors leading to an open balcony overlooking the tennis courts. The enclosed laundry room includes a new washer and dryer. The generously sized kitchen offers a pantry, eat-at bar, and newer appliances, including a dishwasher, oven, and microwave replaced in 2023. Major system updates include a new air conditioner and water heater in 2025. The primary suite is exceptionally large, featuring two a huge walk-in, an additional built-in closet, and a separate linen closet. The en-suite bathroom includes an extra-large walk-in shower and an enclosed commode. Two additional spacious bedrooms share a full tub bathroom and have access to another linen closet. This community has completed all required Milestone & SIRS inspections , all assessments have been paid. The unit also includes two storage spaces, one conveniently located on the same floor and another in the parking garage, ideal for beach or golf equipment. Residents enjoy a beautiful tropical heated pool area. No pets permitted. 1 yr min rental. Membership to Countryside Golf & Tennis is NOT included.
Listing is courtesy of: COLDWELL BANKER REALTY (727-581-9411)
Listing Agent: Lori Balkin (727-365-0078)
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