Location: Clearwater , 33763
Do Not Show Listings
2221 CYPRESS POINT DR E, CLEARWATER, FL 33763
$456,000Listed 04/09/2026 12:18AM MLS ID: TB8490947
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1409 Built: 1986 Tax: $7,580 (2025)Community: Cypress PointSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,580
Elementary School: Leila G Davis Elementary-PN
High School: Dunedin High-PN
Tax Year: 2025
Middle School: Safety Harbor Middle-PN
Remarks: Step inside to a comfortable and inviting living space where a fireplace creates a natural focal point, complemented by a skylight and an abundance of windows that bring in great natural light. Recent updates include a roof installed in March 2026, a 2019 AC system, and a 2018 water heater. The kitchen has been updated with custom wood cabinetry, including a lazy Susan for added storage, pull out shelving in the pantry along with granite countertops and a beautiful tile backsplash. Both bathrooms have been updated within the past four years, and the primary suite includes a private en-suite bathroom. The split-bedroom floor plan offers added privacy, and all bedrooms feature updated luxury vinyl flooring for a clean, modern feel. Just off the kitchen and living room, a covered patio opens to a large, private backyard—offering a great space to relax or entertain. The home also includes a 2-car garage and a dedicated laundry room, adding to the overall functionality. Located in Clearwater, this property offers convenient access to US-19, making commuting throughout Tampa Bay simple. Nearby, you’ll find a variety of shopping and dining options, including Countryside Mall, along with local parks and everyday conveniences. Just a short drive away are some of the area’s most popular Gulf beaches, including Clearwater Beach, Honeymoon Island State Park, and Caladesi Island State Park, known for their white sand and coastal scenery.
Listing is courtesy of: RE/MAX CHAMPIONS (727-807-7887)
Listing Agent: Rachel Mayhew (727-224-5269)
2223 PHILIPPINE DR #35, CLEARWATER, FL 33763
$335,000Listed 04/08/2026 10:09PM MLS ID: TB8493880
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1680 Built: 1993 Tax: $3,954 (2025)Community: On Top Of The WorldCondo
Taxes:$3,954
Elementary School: None
High School: None
Middle School: None
Remarks: Beautifully remodeled condo located in the highly sought-after On Top of the World, a premier 55+ community offering retirement living at its finest! This spacious 2-bedroom, 2.5-bathroom residence features 1,680 heated square feet, making it one of the larger floor plans in the community. Designed for comfort and convenience, this home includes a private in-unit laundry room and is truly move-in ready. Enjoy a long list of brand-new upgrades, including luxury vinyl flooring with sound-reducing underlayment, refinished kitchen cabinets paired with elegant quartz countertops, stainless steel appliances, a new garbage disposal, complete updates in all 3 bathrooms, fresh interior paint, updated electrical outlets, modern LED lighting fixtures, new fans, decorative shutters, and updated plumbing under all sinks with new water shut-offs. Every detail has been thoughtfully updated to provide a modern, low-maintenance lifestyle. The association offers exceptional value, covering exterior building maintenance—including the roof and landscaping—gated security, trash removal, cable TV, and more, giving you peace of mind and easy living. The lifestyle here is truly second to none. Residents enjoy access to two championship golf courses free of charge, two large swimming pools, tennis and pickleball courts, a fully equipped fitness center, hobby studios, a fishing pier, kayaking, a dog park, and a convenient free community shuttle—all just steps from your door. This unit represents an exceptional opportunity to own one of the larger floor plans available in this class of building, ideally situated within one of the most desirable locations in the community. Priced to sell and ready to show. Come experience for yourself why On Top of the World has remained one of Florida’s most beloved active adult communities for decades.
Listing is courtesy of: PREFERRED REALTY GROUP, LLC (727-418-1020)
Listing Agent: Sandy Harris (727-365-3930)
2460 FRANCISCAN DR #16, CLEARWATER, FL 33763
$224,900Listed 04/08/2026 3:58PM MLS ID: TB8494979
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1974 Tax: $766 (2025)Community: On Top Of The WorldCondo
Taxes:$766
Remarks: Beautiful first-floor unit located in the highly desirable On Top of the World community! Enjoy peaceful golf course views right from your back patio, overlooking the 13th and 14th holes. This well-maintained home features an updated kitchen with a newer stove, updated windows, and ceramic tile flooring throughout for easy maintenance and a clean-up. Relax and unwind on either your front or back patio—perfect for enjoying Florida’s sunshine and breezes. Convenient first-floor access makes this unit ideal for comfortable, low-maintenance living. Call today.
Listing is courtesy of: BONOMO REALTY LLC (727-733-3777)
Listing Agent: Susan Manser (813-966-0807)
2295 BELGIAN LN #7, CLEARWATER, FL 33763
$155,000Listed 04/08/2026 3:54PM MLS ID: TB8495529
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1050 Built: 1988 Tax: $2,514 (2025)Community: On Top Of The WorldSpa: NoCondo
Taxes:$2,514
Remarks: Step into easy Florida living with this move-in ready, meticulously maintained, FIRST FLOOR CONDO, perfectly positioned on the desirable Westside of the community! This sought after 1050 sf Supreme model offers comfort and convenience with parking directly out front for easy access. This unit features 2 bedrooms & 2 baths, a living room/dining room combination and a kitchen/great room combination to utilize every square inch to the fullest. Features include NEWER WINDOWS that invite in natural light, INSIDE ALL-IN-ONE WASHER & DRYER for daily ease, FRESH NEUTRAL PAINT, LIGHT & BRIGHT KITCHEN, and a FRONT PORCH & BACK PATIO for relaxing and entertaining. Enjoy the best of resort style living in this vibrant 55+ community, where amenities abound. Located just minutes from the sugar sand shores of the Gulf Coast's world renowned beaches, you'll have paradise right at your fingertips. Value priced & beautifully cared for, this charming condo is your opportunity to make your Florida dream a reality-don't miss it! Assigned parking. The 55+ community has two activity centers, and two private golf courses with 9 and 18 holes, free exclusively for residents & owners. There are two heated swimming pools. The remodeled Cardio Gym has the latest exercise equipment. A very pet-friendly community, there is a fenced dog park with covered seating. There are hobby studios, and a wood shop for the exclusive use of the residents. Activities include fitness classes, dancing, clubs, cards, billiards, entertainment, classes, and much more. The on-site Good Karma Café has take & bake meals and snacks. Close to beaches, transportation, shopping, entertainment, and fine dining. All room sizes, floor plans and square footage are approximate. This property is being transferred by a leasehold estate deed. Association approval is required. If financing, a 35% down payment is required. Washer, Dryer & hook ups must be approved by the association.
Listing is courtesy of: ON TOP OF THE WORLD RE (727-799-3417)
Listing Agent: Shannon Burskey (727-723-5035)
1960 UNION ST #22, CLEARWATER, FL 33763
$170,00034 Days on yellowkey MLS ID: TB8484026
0 Days Off yellowkey (back on 4/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 943 Built: 1976 Tax: $3,670 (2025)Community: Oak Lake Park CondoCondo
Taxes:$3,670
Remarks: Under contract-accepting backup offers. Direct waterfront 2 bedroom, 2 bath condo in Oak Lake Park with beautiful water views from the living area. This bright and inviting unit features updated windows and sliding glass door, newer kitchen and bath fixtures, and an in-unit washer and dryer for added convenience. The spacious layout offers approximately 940 square feet of living space and includes an assigned parking space. Oak Lake Park is a pet-friendly community with amenities including a community pool and peaceful waterfront setting. Located just minutes from downtown Dunedin, shopping, dining, parks, and Gulf beaches, this location offers convenience and the Florida lifestyle. Enjoy low-maintenance condo living in a desirable Clearwater location. Seller welcomes all offers.
Listing is courtesy of: ENRG GLOBAL REALTY, LLC (305-389-2922)
Listing Agent: Dana Murdock (727-300-9257)
2063 PINE RIDGE DR, CLEARWATER, FL 33763
$389,00024 Days on yellowkey MLS ID: TB8487303
REDUCED by $10,000 (2.5%) on 04/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1158 Built: 1962Monthly Fee: $18 Tax: $4,547 (2025)Community: GreenbriarSingle Family
Taxes:$4,547
Elementary School: Garrison-Jones Elementary-PN
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)
2043 DENMARK ST #67, CLEARWATER, FL 33763
$109,90029 Days on yellowkey MLS ID: TB8484459
REDUCED by $3,090 (2.7%) on 04/08/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 825 Built: 1971Monthly Fee: $544 Tax: $1,465 (2025)Community: On Top Of The WorldCondo
Taxes:$1,465
High School: Countryside High-PN
Remarks: PRICE IMPROVEMENT! Yes, a new Price and Priced to Sell...A one bedroom that has all the touches and elements of elegance; Freshly painted throughout, vinyl flooring, upgraded kitchen and bathroom come and see this creatively designed kitchen and bath where no expense was spared in its quartz counter tops, kitchen with artistically appointed hardware, cabinets, dishwasher, frig, new oven and cooktop, crowned by the Microwave with an exhaust fan system, deep and wide kitchen sink, stylish faucets and a dining bar that helps make this stunning room central to the home, accentuating lifestyle and easy living. Its’ bathroom with all new appliances designed with marble tiles in the walk-in shower, gold hardware faucets and shower head, accents that help elevate the environment and lend ease to personal care. All new vinyl flooring throughout with neutral tones that will match any décor you bring in to enhance its beauty. The purchaser of this condo should also know, both the air conditioner and water heater had been replaced within the last 4 years and maintained with longevity in mind. With spa and swimming pools, over 150 clubs to join, bingo every Monday night and tennis, pickle ball and lawn bowling, billiards, and the state-of-the-art fitness facility, this community gives lifestyle to the hundreds of residents who just love living here, joining in on the activities and leisure living at On Top of the World. Welcome Aboard!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Lynda Lafair (727-492-2672)
2231 UTOPIAN DR E #219, CLEARWATER, FL 33763
$225,0001 Day on yellowkey MLS ID: TB8493294
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1210 Built: 1995 Tax: $2,670 (2025)Community: On Top Of The WorldCondo
Taxes:$2,670
Remarks: Step into easy, carefree living with this beautifully maintained 2-bedroom, 2-bath condo located in the highly sought-after On Top of the World 55+ gated community in Clearwater. This bright and inviting home offers 1,210 square feet of living space, a well designed layout featuring a large kitchen, open concept living and dining area, generously sized bedrooms, ample closet space, with an additional storage area for your in-unit washer & dryer—providing both comfort and functionality. Additionally there is 1 assigned parking space and guest parking available. Positioned just east of Belcher Road, this location offers a peaceful setting while still being conveniently close to the community’s outstanding amenities. Residents enjoy access to two golf courses, including both an 18-hole and a 9-hole course, as well as two activity centers that host a wide variety of social events and recreational activities. Stay active in the fully equipped fitness center featuring modern cardio machines, strength training equipment, circuit training, and spinning classes. The community also offers a scenic private park set along a tranquil lake with a walking trail—perfect for enjoying the outdoors. For added convenience, complimentary bus service provides easy access to nearby shopping centers. Ideally located just minutes from Clearwater’s top rated beaches, as well as a variety of dining and retail options, with Publix directly across the street for everyday needs. Whether you’re seeking a full-time residence or a seasonal getaway, this home offers a perfect blend of comfort, convenience, and a vibrant, resort-style lifestyle.
Listing is courtesy of: KELLER WILLIAMS ST PETE REALTY (727-894-1600)
Listing Agent: Jac Smith (727-228-1777)
2549 OAKLEAF LN #36C, CLEARWATER, FL 33763
$269,90013 Days on yellowkey MLS ID: TB8490692
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1011 Built: 1979 Tax: $557 (2024)Community: Village On The GreenCondo
Taxes:$557
Tax Year: 2024
Remarks: Newly remodeled villa providing tranquil views of the community lake. Being an end unit, it provides additional natural light throughout. Updates include open concept kitchen/LR/DR as well as converting exterior sunroom into year-round living space. The kitchen features new, soft-close cabinets topped with quartz countertops along with a custom built-in pantry and a newly added counter peninsula that opens into the LR providing extra cabinets and seating space. There is a newly created ledger-rocked electric fireplace in the Living area that has been structurally designed to hold a wall mount tv and that also includes a built-in heater for those slightly chilly evenings. The bathrooms have been updated with new contemporary tile surrounds, updated vanities and light sources. The flooring throughout the unit is luxury vinyl plank surrounded by 5.25" white baseboards and the walls have been textured to further add a sense of contemporary flair. The ducted sunroom provides a wonderful opportunity for flex space be it office, sitting room, craft room, etc. and has large tinted windows to allow for easy air flow into the unit on those cool spring days. It directly overlooks the outdoor patio which includes a separate area for your addition of a bbq unit. All of this while overlooking a wide open space of lush greenery which also includes peaceful water views. There is extra storage space provided by an outdoor, private storage closet as well as attic space within the unit. Your covered parking spot is just steps away from your front door. The community has a wonderful clubhouse that features a large pool that also overlooks the community lake and provides various social clubs. Village on the Green is located near Countryside Mall and only 10 minutes to downtown, eclectic Dunedin which offers specialty store shopping and restaurants as well as frequent festivals, parades and events which include a weekly outdoor market.
Listing is courtesy of: GULFSHORES REALTY GROUP (727-202-8866)
Listing Agent: Penny Nadar (727-430-9392)
2220 SPANISH DR #14, CLEARWATER, FL 33763
$199,90074 Days on yellowkey MLS ID: TB8468365
REDUCED by $15,100 (7.0%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1994 Tax: $934 (2025)Community: On Top Of The WorldSpa: NoCondo
Taxes:$934
Remarks: 55+ COMMUNITY. Welcome to easy Florida living in the highly sought-after On Top of the World community, located in the Queen Victoria building. This first-floor condo offers the perfect blend of comfort, convenience, and lifestyle set next to Harbor Lake with partial water views right from your front door. Inside, the unit opens directly into the main living area featuring laminate flooring and an open, functional layout. The living room flows seamlessly into the kitchen, creating a welcoming space for everyday living and entertaining. The kitchen is finished with ceramic tile flooring, Corian countertops, and connects effortlessly to the dining area, which also features ceramic tile for durability and easy maintenance. The primary bedroom continues the laminate flooring and includes an en-suite bath with dual sink vanities, offering both comfort and convenience. Additional highlights include a 2025 water heater, in-unit washer and dryer (2025), and a benefit of two outdoor spaces—a front patio plus a rear open deck, ideal for enjoying fresh air and peaceful surroundings. Located within On Top of the World, residents enjoy a resort-style, 55+ lifestyle with access to world-class amenities including multiple golf courses, swimming pools, fitness centers, clubs, social activities, walking paths—all just a short distance away from Clearwater beaches, shopping, and dining. Financing note: If financing, a 35% down payment is required. This is a fantastic opportunity to enjoy low-maintenance living in one of Clearwater’s most established and amenity-rich communities.
Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)
Listing Agent: Jon Mitchell (727-385-7635)
2468 FLORENTINE WAY #34, CLEARWATER, FL 33763
$130,0006 Days on yellowkey MLS ID: TB8491637
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1974Monthly Fee: $545 Tax: $2,182 (2025)Community: On Top Of The WorldCondo
Taxes:$2,182
Remarks: Enjoy peaceful, easy living on a quiet cul-de-sac in the highly desirable 55+ community of On Top of the World, where golf course views and resort-style amenities create the ultimate Florida lifestyle. This light-filled 2-bedroom, 2-bath condo offers a spacious layout featuring a combined living and dining area ideal for entertaining, plus a versatile family/sitting room adjacent to the kitchen for added comfort. The kitchen highlights updated cabinetry and durable ceramic tile floors, while sleek laminate flooring extends through the primary living areas. Freshly painted interiors in the main living areas and bedrooms ensure a unified, turnkey vibe ready for your personal touch. The primary bedroom features an updated private en-suite bath with a walk-in shower and elegant granite countertops. The guest bath, remodeled in 2021, mirrors this style with its own walk-in shower and matching granite countertops for a polished finish. Offered fully furnished, this turnkey residence allows you to move right in and start enjoying the Florida lifestyle from day one. Embrace an energetic, resort-inspired lifestyle with complimentary access to both a 9-hole and 18-hole golf course via the community activity card, plus two heated pools for leisurely swims and unwinding. Keep fit at the on-site fitness center, let your furry friends play at the dedicated dog park, or dive into over 100 clubs and social events that foster lasting connections among neighbors. Conveniently nestled in the heart of Clearwater, you're just minutes away from Clearwater Beach, the eclectic shops and restaurants of Downtown Dunedin, and endless entertainment options-making this the ideal spot to savor Florida's finest offerings. Additional Highlights: HVAC (2019), water heater (2018), stainless steel refrigerator (2019), and Hurricane-impact windows throughout. Note: Buyer approval is required. If financing, On Top of the World requires a 35% down payment.
Listing Agent: Tracey Gendron (813-482-7726)
2416 WORLD PARKWAY BLVD #26, CLEARWATER, FL 33763
$168,000128 Days on yellowkey MLS ID: TB8450929
REDUCED by $2,000 (1.2%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1979 Tax: $2,003 (2025)Community: On Top Of The WorldSpa: NoCondo
Taxes:$2,003
Remarks: PRICE IMPROVEMENT ALERT! Incredible Value in On Top of the World Community! Step into your sun-filled Florida retreat in the highly sought-after 55+ community of On Top of the World where resort-style living meets everyday comfort. This beautifully maintained 2-bedroom, 2-bath condo with nearly 1,400 sq ft is the perfect blend of space, style, and convenience—and now it’s priced to sell! From the moment you walk in you’ll love the bright, open great room—ideal for entertaining or relaxing—featuring elegant wainscoting and charming Tiffany-style lighting that adds a unique touch of character. The oversized primary suite is your private escape with a wall of closets, an updated en-suite bath, and a gorgeous step-in shower. Guests will feel right at home in the spacious secondary bedroom with easy access to a full hall bath. The updated kitchen is a standout offering granite countertops, stainless steel appliances, white cabinetry, modern backsplash, and even a fun chalkboard wall. It opens to a huge 25’ enclosed Florida room perfect for morning coffee, hobbies, or extra entertaining space year-round. Move-in ready with low-maintenance flooring, same-floor laundry just steps away, peaceful golf course views from your front windows all nearby to the pool & community center. The lifestyle is Unbeatable. Enjoy FREE golf, two pools (including heated), fitness center, tennis, pickleball, dog park, hobby clubs, and more—all included in your condo fees along with cable, water, sewer, trash, and maintenance. Located just minutes from shopping, dining, beaches, and parks—this is Florida living at its best! Opportunities like this don’t last, especially at this new price! Schedule your private showing today and make this vibrant, easy-living lifestyle yours.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Barbaranne Hill-Irving (513-319-0581)
2476 ENTERPRISE RD #6, CLEARWATER, FL 33763
$148,00042 Days on yellowkey MLS ID: TB8480142
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 593 Built: 1980 Tax: $1,830 (2025)Community: Villas At Countryside TheVilla
Taxes:$1,830
Remarks: Fully furnished neat and clean 1-bedroom villa centrally-located near the Countryside Mall! This corner unit has windows on three sides (including rear sliding door) and is very light and bright! Very quiet community with pool and no age restrictions - and a low monthly HOA fee that can't be beat! Sit outside in the screened back patio and feel the breeze and be near nature. All exterior maintenance, including roof (replaced in 2023), covered by HOA. Home has been very well maintained. Move-in ready. Bring your clothing and toothbrush. Great for a starter home, or perfect for second home for snowbirds! Come visit today!!!
Listing Agent: Leslie Hobbs (727-365-3650)
2370 JAMAICAN ST #84, CLEARWATER, FL 33763
$159,900280 Days on yellowkey MLS ID: TB8403861
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1978 Tax: $2,038 (2024)Community: On Top Of The WorldCondo
Taxes:$2,038
Remarks: Top-Floor Corner Unit | New A/C 2025 | Optional Furnished | Active 55+ Golf Community Enjoy easy Florida living in this beautifully updated 2-bedroom, 2-bath top-floor corner unit in Clearwater’s highly sought-after On Top of the World community. With no upstairs neighbors and additional windows from its corner location, this light-filled condo offers a quiet, private setting with a spacious and comfortable layout. Recent upgrades provide peace of mind, including brand-new hurricane impact windows and a new A/C system (2025) — major improvements already completed for the next owner. The open living and dining area flows into a functional kitchen with ample cabinetry and storage. Both bedrooms are generously sized, making this home ideal for full-time living or hosting guests. Available furnished (optional), with furnishings negotiable via separate agreement, offering a potential turnkey opportunity for seasonal residents or second-home buyers. Residents of On Top of the World enjoy a highly active and amenity-rich lifestyle, including two private golf courses (free for residents), heated swimming pools, tennis and pickleball courts, a fitness center, hobby studios, and multiple clubhouses with social events and activities. The monthly fee includes cable, internet, water, sewer, trash, exterior maintenance, and grounds care, providing a simplified, low-maintenance lifestyle. Conveniently located near shopping, dining, medical facilities, and just a short drive to Clearwater’s world-famous Gulf beaches. Ideal for cash or strong down payment buyers seeking value, convenience, and an active 55+ community lifestyle.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (813-749-0875)
Listing Agent: Peter Gawienczuk (813-743-4178)
2260 COSTA RICAN DR #6, CLEARWATER, FL 33763
$262,00031 Days on yellowkey MLS ID: TB8484175
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1985 Tax: $3,342 (2025)Community: On Top Of The WorldCondo
Taxes:$3,342
Remarks: One or more photo(s) has been virtually staged. Imagine Coming Home to this beautifully updated unit located on the West side of the desirable On Top of the World 55+ golf community, this 1st-floor, 1,370 sq ft condo offers modern comfort just steps from the West Activity Center & its luxurious heated pool. The home features an updated kitchen with high-quality cabinetry, soft close doors, modern hardware, sleek quartz countertops, brand new Samsung stainless-steel appliances, under-cabinet lighting, and luxury vinyl tile flooring throughout. Updated doors & Updated windows paired with plantation shutters provide both style and energy efficiency, while fresh interior paint and ceiling fans add to the move-in-ready appeal. Both bathrooms have been tastefully updated, including a New Vanities, Commodes & Lightning. The primary bedroom offers an En suite' bathroom and exceptional storage with closet organizers, mirrored closet doors, a built-in storage unit, and a charming window seat that adds both character and functionality. Enjoy the convenience of front and back porches, perfect for relaxing outdoors, along with the added peace of mind of hurricane shutters. Newer A/C & Tankless Water Heater. The convivence of your parking space right outside your door makes it perfect. This thoughtfully improved home combines comfort, functionality, and an unbeatable location within one of Clearwater’s most active and welcoming 55+ communities.
Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)
Listing Agent: Lynne Leida-Goldsmith, Pa (727-410-9099)
2220 SWEDISH DR #56, CLEARWATER, FL 33763
$214,00062 Days on yellowkey MLS ID: TB8472270
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1440 Built: 1991 Tax: $501 (2024)Community: On Top Of The WorldCondo
Taxes:$501
Remarks: One or more photo(s) has been virtually staged. Step into this light-filled 2-bedroom, 2-bath condo on the West Side of Clearwater’s highly desirable On Top of the World 55+ Golf Community. Located on the second floor, this home immediately impresses with its cathedral ceilings, Updated HURRICANE Impact resistant windows creating a bright, open, and airy atmosphere. Vinyl plank flooring throughout adds a clean, modern finish. The spacious gathering room is ideal for relaxing or entertaining, enhanced by updated windows that flood the space with natural light. The kitchen includes a new refrigerator, and the convenience continues with an in-unit washer and dryer. The 2017 A/C offers reliable comfort and peace of mind. The primary bedroom features an en suite bath with a bidet, providing privacy and comfort. Just outside your front door, enjoy a charming sitting area—perfect for morning coffee or evening breezes—along with beautiful views that make this location feel special. BRING ALL REASONABLE OFFERS. Additional storage in the core of the building gives you extra room for seasonal items or personal belongings. Situated on the west side of the community, you’ll appreciate being close to Harbor Lake, scenic walking trails, and all the amenities that make OTOW such a sought-after lifestyle—golf, clubs, activities, and more.
2016 SUNSET MEADOW DR, CLEARWATER, FL 33763
$319,00033 Days on yellowkey MLS ID: TB8483594
REDUCED by $6,000 (1.8%) on 04/08/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1274 Built: 2007Monthly Fee: $414 Tax: $2,361 (2025)Community: Sunset Pointe TwnhmsTownhouse
Taxes:$2,361
Remarks: LOCATION! LOCATION! LOCATION! BEAUTIFUL, SAFE, FAMILY-FRIENDLY, AND PET-FRIENDLY COMMUNITY! SPACIOUS OPEN FLOOR PLAN! IDEALLY LOCATED RIGHT IN FRONT OF THE COMMUNITY POOL! Lovingly maintained by the same owner for the past 8 years, this move-in ready 2-bedroom, 2.5-bath townhome with ATTACHED GARAGE and OPEN FLOOR PLAN is located just steps from the community pool. The first floor features laminate flooring and a spacious living/dining room combo that flows into the kitchen with breakfast bar and ample counter space. Sliding doors lead to a private partially fenced patio with no rear neighbors, DUKE ENERGY TRAIL IS RIGHT BEHIND THE PATIO!!! Perfect for walking, running, or biking. Upstairs offers two spacious bedrooms, two full bathrooms, and inside laundry. The primary suite features a tray ceiling, walk-in closet, and ensuite bath with separate bath tub,walk-in shower and double vanity!!! Low HOA fee includes CABLE, INTERNET, ROOF, GARBAGE, EXTERIOR MAINTENANCE, LAWN, PLAYGROUND AND POOL. NO FLOOD ZONE, NON-EVACUATION ZONE. This home is ideally located just minutes from multiple grocery stores, including ALDI, PUBLIX, SPROUTS, WHOLE FOODS, WORLD MARKET, and WALMART. COUNTRYSIDE MALL is less than 10 minutes away, while CLEARWATER BEACH and HONEYMOON ISLAND STATE PARK are both only about 9 miles away. The community is beautiful, safe, family-friendly, and pet-friendly, and offers amenities such as a playground and pool, creating a wonderful setting for outdoor fun and relaxation. Popular CELEBRATION STATION is less than 5 minutes away, adding even more convenience and entertainment for families.
Listing is courtesy of: LLOYD REALTY (727-543-4748)
Listing Agent: Lyudmila Ivanenko (727-656-0787)
2400 COLUMBIA DR #18, CLEARWATER, FL 33763
$214,90035 Days on yellowkey MLS ID: TB8483456
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1972 Tax: $3,054 (2025)Community: On Top Of The WorldSpa: NoCondo
Taxes:$3,054
Remarks: FIRST FLOOR 2 bed/2 bath, directly across from the East Activity Center! As an added bonus, your reserved parking spot is located right in front of your door. Upon entering, the new waterproof wood-based laminate flooring will capture your attention. NO CARPET ANYWHERE! The fresh paint throughout provides a clean, refreshed feel. The spacious primary bedroom features an en-suite bath including a new faucet, and elevated toilet. Both bedrooms include generous closet space. Enjoy peace of mind with updated rear windows that enhance energy efficiency and comfort. Relax and unwind on either your front or back patio, take your pick! HVAC replaced in 2014. Don't delay, schedule your private showing today! Assigned parking. The 55+ community has two activity centers, and two private golf courses with 9 and 18 holes, free exclusively for residents & owners. There are two heated swimming pools. The remodeled Cardio Gym has the latest exercise equipment. A very pet-friendly community, there is a fenced dog park with covered seating. There are hobby studios, and a wood shop for the exclusive use of the residents. Activities include fitness classes, dancing, clubs, cards, billiards, entertainment, classes, and much more. The on-site Good Karma Café has take & bake meals and snacks. Close to beaches, transportation, shopping, entertainment, and fine dining. All room sizes, floor plans and square footage are approximate. This property is being transferred by a leasehold estate deed. Association approval is required. If financing, a 35% down payment is required.
Listing Agent: Carrie Moreno (727-433-2657)
2171 SCOTLAND DR, CLEARWATER, FL 33763
$375,0007 Days on yellowkey MLS ID: TB8492471
1 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1109 Built: 1971 Tax: $2,438 (2025)Community: GreenbriarSingle Family
Taxes:$2,438
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)
2452 ENTERPRISE RD #15, CLEARWATER, FL 33763
$172,00034 Days on yellowkey MLS ID: TB8483107
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 817 Built: 1984 Tax: $2,640 (2025)Community: Villas At Countryside TheCondo
Taxes:$2,640
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this bright and inviting condo nestled in the Villas at Countryside community, located in the heart of the desirable Countryside area of Clearwater. This one level living residence features a functional open floor plan that seamlessly connects the living and dining areas, creating a comfortable and practical living space. Well equipped kitchen with newly installed wood cabinetry, custom granite counter tops, perfect for everyday cooking and entertaining, and stainless-steel appliances. The utility closet houses a state-of-the-art full-size washer and dryer. A tastefully finished bathroom with quality fixtures and custom touches. High quality laminate flooring and neutral paint finishes throughout. Newly installed (2024) high impact windows with transferable warranty, and a newly installed new storm door (2025). A standout feature is the 8’ x 23’ screened-in Florida room (with newly installed sunshades), which adds significant living space and natural light and is not included in the interior square footage. The Villas at Countryside is a well-maintained established community offering: Parking: includes one assigned covered parking space under the carport. Recreation: Residents have access to a heated community pool, clubhouse and shuffleboard courts, a social committee who hosts monthly events for the community (adults and their families). Maintenance Fees: monthly fee includes water, sewer, trash, exterior maintenance: building, pool, grounds, common areas and building insurance. Pet friendly community. Not in a flood zone. MILESTONE INSPECTION COMPLETED. FULLY FUNDED RESERVES. This property is adjacent to Woodgate Park, which offers tennis courts, soccer fields and a playground. Minutes to Countryside Mall and roughly 20 minutes from Clearwater Beach. Conveniently located near US 19, providing easy access to Dunedin, Safety Harbor, Tampa International Airport and Clearwater St. Petersburg Airport.
Listing is courtesy of: CENTURY 21 COASTAL ALLIANCE (727-867-8633)
Listing Agent: Gabrielle Bettig (727-385-9017)
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