Location: Clearwater , 33763
Do Not Show Listings
2310 DENMARK ST #46, CLEARWATER, FL 33763
$145,000144 Days on yellowkey MLS ID: TB8466419
1 Days Off yellowkey (back on 5/29/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1977 Tax: $1,932 (2024)Community: On Top Of The WorldCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,932
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Welcome home to your impeccably clean & maintained 2nd floor condominium at On Top Of The World! This roomy condo is cheerful, sunny & move in ready! Furnished condo includes a queen size hide-a-bed in the living room for extra guests. The floorplan features a spacious & charming combined living/dining area, with wood look laminate flooring. The kitchen is light & bright with vinyl flooring & newer ceiling light. The owners added a sweet kitchen cabinet around the refrigerator for extra storage & display, with a quartz counter-top. The sunlit breakfast room adjoins a cozy Florida room with a newer ceiling fan. The primary bedroom has an en suite for your convenience and privacy, including a tiled step-in shower. The second bathroom has its own bathtub. This condo features Home Depot installed PGT Vinyl Windows in the family room, living room, bathroom and 2nd bedroom for your peace of mind. Windows have a transferable limited warranty. Upgraded tankless hot water system delivers continuous hot water while keeping energy bills low. On Top of the World is a lively 55+ gated, pet friendly golf community. Amenities include 2 Golf Courses (18-hole and 9-hole), as well as 2 Pools (one heated), Sauna, Hot Tub, computer room, library, cafe, dog park, woodworking shop, lawn bowling, walking trails, pickleball and tennis courts! The newly remodeled Cardio Gym is equipped with up-to-date exercise machines. Lots of entertainment here and numerous clubs to have fun with friends. Less than 30 minutes away from the famous Clearwater Beach, 15 minutes away from downtown Dunedin, and 5 minutes from Countryside Mall. Overall, this is a great property to call home! Don't miss out on this Sunshine State gem!
Listing is courtesy of: LIPPLY REAL ESTATE (727-314-1000)
Listing Agent: Joe Gibbons (727-688-0699)
24862 US HIGHWAY 19 N #3002, CLEARWATER, FL 33763
$89,900248 Days on yellowkey MLS ID: TB8435305
REDUCED by $9,000 (9.1%) on 05/29/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1979 Tax: $140 (2024)Community: Hill Crest VillasVilla
Taxes:$140
Remarks: GREAT PRICE!!!!!!!NO LAND LEASE villa style condo in the back of the community offering tons of privacy, peace and quiet. This 600 sq.foot unit @ Clearwater's Hill Crest Villas feels much larger with the additional back bonus Florida Room adding approximately 150 sq. feet. This villa has a FULL SIZED washer and dryer too!! Matched tile floor thruout entire unit gives it a seamless vibe. Bedroom floor is ready for resurfacing. There is NO CARPET in entire home. 2 large closets in bedroom allow plenty of room for all your fabulous fashion options. IMPACT Windows installed in 2018. Custom shower insert and granite topped vanity in bath. Attic storage for all your extras. Covered parking directly at your front door keeps car cool, clean and dry. HUGE and sunny community pool with adjacent clubhouse. Hill Crest is a wonderful all-ages and pet friendly community located literally in the middle of everything. 10 minutes to Safety Harbor, 10 minutes to Dunedin, 10 minutes to downtown Clearwater, walk to Phillies Spring training, 6 blocks to world class shopping and dining @ The Countryside District featuring BJ's Brewhouse, PF Changs, Grillsmith, CHEESECAKE FACTORY, Homegoods, TJ Maxx, WHOLE FOODS, Dillards, MACYS and so much more. Aldi grocery store is LITERALLY next door, so no need to get in the car. PERFECT home for snowbirds, downsizer's, first timer's. NON EVACUATION ZONE and NON FLOOD ZONE! ON SITE management keeps the property in tip top condition. Monthly fee includes cable, roof, internet, pool, manager, lawn care, trash, clubhouse, exterior maintenance, exterior pest control. AC recently had a check up, and its running FROSTY cold! Pinellas trail literally in the backyard for biking or walking. This unit is ready for its next owner's vision. Priced right and waiting for you!!!
Listing is courtesy of: GALLERY PROPERTIES INTERNATIONAL (727-726-3333)
Listing Agent: Ted Ciske (727-385-9192)
2472 ENTERPRISE RD #6, CLEARWATER, FL 33763
$174,900219 Days on yellowkey MLS ID: TB8446261
REDUCED by $5,000 (2.8%) on 05/29/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 817 Built: 1980 Tax: $3,072 (2024)Community: Villas At Countryside TheCondo
Taxes:$3,072
Remarks: LOCATION..LOCATION..LOCATION* Villas of Countryside close proximity to countryside mall, and minutes to the airport or beaches. Corner unit with covered parking near your front door* Freshly painted unit with vinyl flooring throughout unit* nice screened in porch* stainless steel appliances* granite countertops* inside utilities offers a washer and dryer* central heat and air* Pet friendly and NOT a 55+ community* community pool*
Listing is courtesy of: 1ST CLASS REAL ESTATE LLC (727-797-7500)
Listing Agent: Michael Spithoyanis (727-418-9694)
2285 ISRAELI DR #17, CLEARWATER, FL 33763
$185,00050 Days on yellowkey MLS ID: TB8501674
REDUCED by $14,000 (7.0%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1979 Tax: $2,293 (2025)Community: On Top Of The WorldCondo
Taxes:$2,293
Tax Year: 2025
Remarks: One or more photo(s) has been virtually staged. Opportunity knocks! Here we have a first (1st) floor, wheel-chair accessible (ramps are removable), 1400 Sq. Ft., 2-bedroom, 2 full bath, F-Deluxe layout, condominium located in the desirable "On Top of the World" 55+ Golfing Community where owners golf for free. Beautiful Golf course views from the back patio. The flooring is luxury waterproof vinyl throughout the living room into the Florida Room. Ceramic tile flooring in each bedroom and bathroom. Updated bathroom vanities and master shower which is newly tiled. Updated wood kitchen, soft-touch drawers and roll-out shelving, Schuler Cabinetry, solid countertops with plenty of storage space and shelving; it also has newer stainless appliances. The unit includes a ventless washer/dryer combo installed in 2023. The unit has a FRONT and BACK patios (Aluminum Awning on back patio installed 2025). Both patios are sheltered and can be enjoyed rain or shine and there is usually a cool breeze when enjoying the front patio. This is a beautiful home you do not want to miss. On Top of the World is a 55+, golfing community. It has two (2) golf courses, one 18 hole, the other 9 hole. You can enjoy access to two heated pools, state-of-the-art cardio fitness gym, tennis, pickle ball courts, as well as two recreation centers that provide year-round entertainment and a plethora of clubs and activities for almost every interest and hobby. Additionally, the community is close to airports, shopping and professionals of all needs and just 20 minutes away from the most beautiful Gulf Beaches in the nation. (note: some pictures are virtually staged to show potential)
Listing is courtesy of: BONOMO REALTY LLC (727-733-3777)
Listing Agent: Denise Wilder (727-742-6830)
2153 KARAN WAY, CLEARWATER, FL 33763
$960,00017 Days on yellowkey MLS ID: TB8513401
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2867 Built: 1985 Tax: $6,138 (2025)Community: Marla Grove EstatesSingle Family
Taxes:$6,138
Remarks: Welcome to a truly one-of-a-kind waterfront retreat in unincorporated Clearwater’s desirable Marla Groves Estates near Dunedin. Situated on over half an acre along the shores of Harbor Lake, this fully renovated and professionally furnished property offers an exceptional blend of luxury living, resort-style amenities, and proven income potential, while also offering the rare benefit of being located outside of a flood zone with no HOA restrictions. Extensively renovated and transformed in 2025 with upgrades including a new roof (including flat roof), newly resurfaced pool, and brand-new pool heater, this expansive residence features 4 bedrooms plus an enclosed sunroom/office, 3 bathrooms, and approximately 2,867 square feet of thoughtfully designed living space curated for both everyday comfort and unforgettable entertaining. Vaulted ceilings, hardwood flooring, designer finishes, two stunning stone fireplaces, and multiple indoor-outdoor gathering spaces create a warm yet elevated atmosphere throughout the home. Step outside into your own private lakeside oasis featuring a heated pool, expansive entertaining areas, mature landscaping, and direct access to Harbor Lake — a rare 40-acre spring-fed lake where boating, kayaking, and fishing are permitted. The oversized fenced lot includes abundant parking with room for guests, boats, RVs, and recreational vehicles. The spacious primary suite and additional upstairs bedroom open to a large screened balcony overlooking the pool and lake, offering breathtaking sunset views and a true retreat-like experience. Whether used as a full-time residence, second home, luxury vacation property, or income-producing short-term rental, this property offers unmatched versatility. This home is currently operating as a successful high-performing Airbnb with Guest Favorite and Superhost status. Furnishings available separately for purchase, making this a potential turnkey opportunity for buyers interested in continuing short-term rental operations. Ideally positioned near Dunedin, Clearwater Beach, Honeymoon Island, MLB Spring Training fields, golf courses, shopping, dining, and Tampa International Airport. This exceptional property delivers the best of Florida waterfront living with privacy, flexibility, and lifestyle at its core. Rarely does a property combine this level of location, land, water access, renovation quality, and income potential in one offering.
Listing is courtesy of: REALTY EXPERTS ASSOCIATES (727-614-0105)
Listing Agent: Jennifer Mcdonnell (727-247-2896)
2220 SPANISH DR #54, CLEARWATER, FL 33763
$185,00055 Days on yellowkey MLS ID: TB8499807
REDUCED by $10,000 (5.1%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1994 Tax: $1,693 (2024)Community: On Top Of The WorldSpa: NoCondo
Taxes:$1,693
Remarks: Nestled on the peaceful cul-de-sac of the newer Westside of On Top of the World, this spacious third-floor condo offers 1400 square feet of comfortable living space. Featuring 2 bedrooms and 2 bathrooms, this home is ideal for those seeking a serene retreat. Enjoy vaulted ceilings that create an airy atmosphere, along with beautiful wood floors that add warmth and character throughout. The convenience of an in-unit washer/dryer adds ease to everyday living. Step outside the front door and be greeted by a lovely view of the lake, perfect for relaxing or unwinding after a long day. This condo is priced to sell and offers the ideal combination of space, style, and tranquility. Don't miss out on this amazing opportunity! Assigned parking. The 55+ community has two activity centers, and two private golf courses with 9 and 18 holes, free exclusively for resident 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 is courtesy of: ON TOP OF THE WORLD RE (727-799-3417)
Listing Agent: Carmencita Potesta (727-504-3927)
2360 IRISH LN #16, CLEARWATER, FL 33763
$155,700101 Days on yellowkey MLS ID: TB8483337
REDUCED by $3,800 (2.4%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1978Monthly Fee: $546 Tax: $2,472 (2025)Community: On Top Of The WorldCondo
Taxes:$2,472
Remarks: FIRST FLOOR RELAXATION CENTER**Washer/Dryer connection**Updated Windows***Enjoy your evenings sitting on the front porch and talking to your neighbors. Maybe you would prefer to sit out back on the rear patio and read a book or cook a hamburger on your grill. If you prefer, you can stay inside and simply relax in your condo. You will have Vinyl Manufactured flooring in the living area and carpet in the bedrooms, Association approved Washer/Dryer hookup, Electric Range for cooking, hurricane impact windows in the front and back, semi-updated Master and guest Bath, and of course parking right outside the front door of your Condo. Take advantage of the community and enjoy the many amenities that are provided to you by the On Top of the World Complex. Farmer’s Market, Tennis, Golf, Pickelball, two Swimming Pools, Shuffle Board, Horseshoes, Lawn Bowling, Pet Park, Table Tennis, Billiard room with ten tables, Theatrical plays and Musical Entertainment, Travel Club, Community Bus to get you “to and from” Stores and Appointments, Fitness Center, and Clubs for everyone’s enjoyment, as well as Bridge, Pinochle, Euchre, Hearts, Poker and more for the Card Game enthusiast...
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Tim Richardson (281-865-0333)
2291 AMERICUS BLVD W #37, CLEARWATER, FL 33763
$169,90081 Days on yellowkey MLS ID: TB8490682
REDUCED by $20,000 (10.5%) on 05/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1210 Built: 1993 Tax: $2,898 (2025)Community: On Top Of The WorldCondo
Taxes:$2,898
Remarks: Come and see this top floor unit that features vaulted ceilings for that added feeling of spaciousness and features a direct view of the pond where you can sit and watch the wildlife and walk around the pond on a sidewalk. The unit features a brand-new floor with the look of wood and inside laundry. This is a golf course guard-gated community where you can golf free every day on 27 holes. There is a clubhouse with many planned activities and a heated pool. 55+, land is leased and large pets are OK.
Listing is courtesy of: REAL ESTATE FIRM OF FLORIDA, LLC (727-584-8480)
Listing Agent: Thomas Varga (727-946-8100)
1949 PINEHURST DR, CLEARWATER, FL 33763
$270,00089 Days on yellowkey MLS ID: TB8486602
REDUCED by $15,000 (5.3%) on 05/28/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1095 Built: 1954 Tax: $4,125 (2025)Community: Lake Pines EstatesSpa: NoSingle Family
Taxes:$4,125
Elementary School: Garrison-Jones Elementary-PN
High School: Dunedin High-PN
Middle School: Dunedin Highland Middle-PN
Remarks: Back on the market with a new price improvement. This 2-bedroom, 1-bath Clearwater home offers a strong value-add opportunity in a quiet residential neighborhood just about 10 minutes from Downtown Dunedin and Downtown Clearwater. The home features an open floor plan, stainless steel kitchen appliances, ample kitchen workspace, a fireplace in the main living area, natural light, and comfortable bedroom sizes. The flexible layout offers room to personalize, improve, and create long-term value. The property is priced to reflect needed improvements, giving investors, renovators, and buyers using renovation financing a clear path to add value. Conveniently located near Countryside Mall, Celebration Station, grocery stores, shopping, dining, parks, and everyday essentials. Bring your renovation plan and take a closer look.
Listing is courtesy of: GULF SHORES REALTY ERA POWERED LLC (813-636-0700)
Listing Agent: Filip Cerovic (813-613-9778)
2027 SETON DR, CLEARWATER, FL 33763
$385,00023 Days on yellowkey MLS ID: TB8510989
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $15,000 (3.8%) on 05/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1410 Built: 1971 Tax: $3,729 (2025)Community: Montclair Lake EstatesSingle Family
Taxes:$3,729
Elementary School: Dunedin Elementary-PN
Remarks: Welcome to this charming 3-bedroom, 2-bath home in the desirable Montclair Lake Estates community of Clearwater! Offering a split floor plan in the living space, this single-story residence features a functional layout with NEW central A/C (2026), a spacious attached garage, and a blend of tile, wood laminate, and carpet flooring throughout. The stucco exterior, gabled roof (2019), and mature landscaping create inviting curb appeal, while the unique garden and additional side and rear walkways add character and outdoor enjoyment. Situated on a generously sized lot, this property offers plenty of room for entertaining, gardening, or simply relaxing in your private backyard setting. Conveniently located near Dunedin shopping, dining, parks, top-rated schools, and just a short drive to Clearwater’s world-famous beaches, this home is a fantastic opportunity for first-time buyers, seasonal residents, or anyone looking to enjoy the Florida lifestyle. Don’t miss your chance to make this Clearwater gem your own!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Kevin Orantes (727-656-5152)
2430 FLORENTINE WAY #58, CLEARWATER, FL 33763
$159,90059 Days on yellowkey MLS ID: TB8498394
REDUCED by $8,600 (5.1%) on 05/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1974 Tax: $2,663 (2025)Community: On Top Of The WorldCondo
Taxes:$2,663
Remarks: Discover resort-style living in this stunning TOP FLOOR condo, boasting front GOLF COURSE VIEWS and rear WOODED VIEWS. Upon entering this sun-drenched unit, you are welcomed by a bright and open living room and dining room combo. The chef’s kitchen boasts gleaming NEW countertops, a shining backsplash that complements the newer stainless steel appliances, updated flooring, and crisp, white cabinets with fresh hardware for tons of storage and space to cook and entertain. The spacious primary bedroom offers huge built-in closets and a private, updated EN-SUITE BATH complete with gorgeous newer counters, sinks, hardware, and fixtures, including a low-profile ceiling fan for added comfort. The second bedroom also has tons of storage; both bedrooms feature lush carpet and are bright and sunny. The second bathroom has a new sink, faucet, and a white tub for soaking. The spacious and sun-drenched Florida room boasts IMPACT RATED NEWER WINDOWS and offers amazing lush green wooded views. Modern conveniences include a smart thermostat and an electronic door lock. On Top of the World delivers resort-style living with TWO EXCLUSIVE GOLF COURSES, 9 and 18 holes free to resident owners, TWO HEATED SWIMMING POOLS, tennis, pickleball, a fitness center, DOG PARK, horseshoe pits, lawn bowling, and shuffleboard. A grand ballroom hosts live music and events, and an on-site café offers take-and-bake meals. On Top of the World has over 100 clubs and activities. Milestone Engineering Study passed with flying colors.Ideally located near Dunedin’s beaches, Clearwater Beach, upscale shopping, healthcare, and Tampa International and St. Pete/Clearwater Airports. Seize this chance for luxurious, active living in a vibrant community, SAFELY OUTSIDE OF FLOOD AND EVACUATION ZONES. 35% down required by OTOW if financing.
Listing is courtesy of: PRISTINE FLORIDA PROPERTIES LLC (727-510-8226)
Listing Agent: Anna Smith (309-530-8399)
1960 UNION ST #28, CLEARWATER, FL 33763
$164,90075 Days on yellowkey MLS ID: TB8492216
2 Days Off yellowkey (back on 5/28/2026)
REDUCED by $5,100 (3.0%) on 05/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1049 Built: 1979 Tax: $966 (2025)Community: Oak Lake Park CondoCondo
Taxes:$966
Remarks: Under contract-accepting backup offers. Tucked away from the main road in the quiet, pet-friendly community of Oak Lake Park, this second-floor condominium offers both privacy and everyday convenience with no age restrictions. Fresh exterior paint and brand-new roofs were completed in 2024, giving the community a clean, updated feel and added peace of mind. This unit overlooks the sparkling community pool, just steps from your sliding glass doors. The kitchen features a pass-through window to the living area, creating an open, connected flow that’s ideal for entertaining. Wood laminate flooring runs throughout, offering a stylish look with easy maintenance. The living room opens to a screened lanai with relaxing poolside views, while a split floor plan provides added privacy between the generously sized bedrooms. The primary suite includes a walk-in shower, and the guest bathroom offers a tub/shower combination. An interior laundry and utility room adds everyday convenience and includes a water softener system. The monthly condo fee includes water, sewer, and trash. The unit includes one assigned parking space near the building along with ample guest parking. Residents also enjoy access to a scenic pond and dock, perfect for fishing or unwinding outdoors. Ideally located just minutes from downtown Dunedin, downtown Clearwater, shopping, and the Gulf beaches, this home offers exceptional convenience. Competitively priced to reflect current market conditions, this is a great opportunity for buyers seeking value in a desirable location. Schedule your private showing today.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tulio Zuloaga (727-403-0985)
2284 OAK NECK RD #F, CLEARWATER, FL 33763
$184,900143 Days on yellowkey MLS ID: TB8465972
0 Days Off yellowkey (back on 4/20/2026)
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 825 Built: 1974 Tax: $938 (2025)Community: Laurelwood CondoCondo
Taxes:$938
Elementary School: Leila G Davis Elementary-PN
High School: Countryside High-PN
Middle School: Safety Harbor Middle-PN
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price Improvement! Comfort and Convenience Live Here—Why Not You?? Discover your private retreat in Clearwater’s desirable and quaint Laurelwood community, this one bedroom, one and a half bath is ready for you to move in and start enjoying Florida living. Bright and airy, the open-concept layout blends style and functionality, Indoor and outdoor living spaces connect seamlessly here. Sliding glass doors lead to a spacious private patio—your very own Florida “backyard” oasis. The generously sized primary suite also opens to this outdoor patio space. Tile flooring is featured throughout the condo. The kitchen features marble counters and stainless appliances Plenty of cabinet space and a pantry storage. Both bathrooms are modern. Recently installed windows are PGT impacted rated, other details enhance everyday comfort: the laundry closet can accommodate a full-size washer and dryer, a dedicated covered carport, and a separate storage closet just steps away. The Laurelwood community is beautifully maintained, with lush landscaping, abundant guest parking, and a sparkling pool. HOA fees include water, sewer, trash, cable, exterior upkeep, and more for truly low-maintenance living. Ideally situated near Countryside Mall, top-rated restaurants, boutique shopping, and just minutes from Downtown Dunedin, Award Winning Gulf Beaches, and Honeymoon Island State Park, this home offers the perfect mix of serenity and convenience. Whether you’re looking for a year-round residence or seasonal escape, this should be your new home! Schedule your showing today! One or more photos have been virtually staged. Amenities include a beautiful pool and a assigned carport with plenty of guest parking.
Listing is courtesy of: CELTIC REALTY (727-412-8558)
Listing Agent: David Vose (727-798-9158)
2383 NETHERLANDS DR #57, CLEARWATER, FL 33763
$145,00018 Days on yellowkey MLS ID: TB8511926
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1982Monthly Fee: $563 Tax: $2,723 (2025)Community: On Top Of The WorldCondo
Taxes:$2,723
Remarks: Newly Renovated, New AC System, new paint all over and updated kitchen. Step into a realm of active living and boundless enjoyment within the distinguished “On Top of The World” 55+ community that stands as a testament to vibrant and engaging retirement. This exceptional haven, set against the backdrop of convenience and beauty in Clearwater presents an array of amenities that weave together a tapestry of unparalleled experiences minutes away from beaches, shopping and restaurants. this exquisite 2-bedroom, 2-bathroom condo embodies the essence of retirement living at its finest. Featuring luxury laminate flooring, Kitchen granite countertops. This unit resides on the third floor, presenting a unique perspective on community living. Here, residents are gifted with a sense of elevation, both literally and metaphorically. The sights and sounds of the neighborhood meld harmoniously, allowing for a retreat into serenity while remaining connected to the vibrant pulse of the community. Imagine a place where not one, but two vibrant activity centers come alive with the energy of residents pursuing their passions. As an exclusive privilege for resident owners, two private golf courses weave through the landscape, one boasting 9 holes and the other, a grand 18 holes. A haven for golf enthusiasts, these courses embrace the thrill of the game and the beauty of the outdoors. The allure of relaxation takes shape through the ripple of pristine waters in two inviting swimming pools. While one pool welcomes you to bask in its warmth, the other refreshes with invigorating coolness. But the story doesn't end there—step into a remodeled Cardio Gym, where the latest exercise equipment stands ready to invigorate both the body and spirit. This community wears its pet-friendly badge with pride, offering a haven for four-legged companions within a fenced dog park accompanied by sheltered seating. And for the creatively inclined, the embrace of community extends to hobby studios and a well-stocked wood shop. Here, craftsmanship is nurtured, artistic pursuits thrive, and the bonds of shared interests are formed.
Listing is courtesy of: LAUREN MICHAELS R.E. PARTNERS (727-298-8888)
Listing Agent: Shady Messiah (727-688-5719)
2370 JAMAICAN ST #84, CLEARWATER, FL 33763
$159,900346 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)
2554 SEA WIND WAY, CLEARWATER, FL 33763
$280,00050 Days on yellowkey MLS ID: W7885203
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1252 Built: 2007Monthly Fee: $414 Tax: $4,453 (2025)Community: Townhome Manors OfSpa: NoTownhouse
Taxes:$4,453
Remarks: 2 Bedrooms with 2 Full Bathrooms, Townhome located in Clearwater, positioned in a Non-Flood Zone per the county, offering added peace of mind. The layout provides a functional use of space with comfortable living areas and natural light throughout. Set in a convenient location with easy access to shopping, dining, and major roadways, making everyday travel simple. The surrounding area offers a quiet residential feel while still being close to the beaches, parks, and all that Florida’s Gulf Coast lifestyle has to offer. The HOA is well-regarded by residents and provides true low-maintenance living and includes exterior maintenance, grounds upkeep, common areas, trash service, cable TV, and high-speed internet. Residents also enjoy access to a community pool and playground, making it easy to relax and enjoy Florida living without the upkeep of a single-family property. Even better, grilling in the backyard is permitted, so enjoying Florida evenings with friends and family is easy. Conveniently located near shopping, dining, beautiful Gulf beaches, and just minutes to PIE and Tampa International Airport, this home offers both comfort and convenience in one compelling Clearwater opportunity. Community is not age-restricted. Rental restrictions apply (no leasing within the first two years of ownership). 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)
2428 COLUMBIA DR #22, CLEARWATER, FL 33763
$159,90060 Days on yellowkey MLS ID: TB8497611
REDUCED by $20,100 (11.2%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1972 Tax: $2,457 (2025)Community: On Top Of The WorldCondo
Taxes:$2,457
Remarks: GROUND FLOOR WITH PARKING RIGHT IN FRONT!!!!!! Better be quick to this 2/2 with a sunroom, this beautiful condo is move in ready, light and bright, and best of all its on the ground floor. Active 55 plus community, 2 golf courses, two activity centers with pools, sauna, fitness center, tennis/pickleball courts, lawn bowling, shuffleboard, woodworking shop, billiards room, dancing auditorium with shows, lots of community classes, social events, Good Karma Cafe, library, bbq area.. busses for transportation to shopping, a lake with a fishing pier and kayaking, dog park with covered seating. This property is centrally located to shopping, airports, churches, hospitals, beaches, restaurants, don't miss out for this price!!!
Listing Agent: Kirk Budd (727-433-2947)
2370 JAMAICAN ST #54, CLEARWATER, FL 33763
$160,000157 Days on yellowkey MLS ID: TB8460873
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1978 Tax: $482 (2024)Community: On Top Of The WorldCondo
Taxes:$482
Remarks: Beautiful Condo in Clearwater’s Premier 55+ Golf Community. Move right into this 2-bedroom, 2-bath 2nd-floor unit located in the highly desirable On Top of the World community. Upgrades Include new double-pane, hurricane impact resistant windows. Inside, you'll find an open floor plan with a bright living area, dedicated dining space, and a kitchen with new refrigerator and dishwasher, oak cabinets. Comfortable back room to sit and read a book or work on your hobby. Open the rear window to get a good breeze as you over look the large grassy outdoor space. Enjoy doing your laundry at your leisure with your own washer dryer. The large bedrooms are excellent for residents and guests alike with the convenience of a private bath in the Primary bedroom. Residents enjoy an unmatched lineup of amenities in this active 55+ community: Two private golf courses (no fee for residents), Two heated swimming pools, Tennis & pickleball courts, State-of-the-art fitness center, Two clubhouses that entertain social events, classes, clubs & dances. Also, available is a hobby studio, a woodshop, a dog park, walking trails, and more. Included in the HOA: Water, sewer, trash, cable TV, internet, exterior maintenance, grounds care, and full access to all community amenities. Pet-friendly community. Prime Clearwater Location: Just minutes to the beautiful Gulf beaches, shopping, dining, evening entertainment and medical facilities, and transportation options. This condo has exceptional value with an unbeatable lifestyle in one of Florida’s most sought-after 55+ communities. Bring your decorating ideas to make this place your home!!!
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Tim Gorr (727-804-0732)
2258 WORLD PARKWAY BLVD W #56, CLEARWATER, FL 33763
$149,90072 Days on yellowkey MLS ID: TB8493846
2 Days Off yellowkey (back on 5/27/2026)
REDUCED by $5,000 (3.2%) on 05/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1400 Built: 1983 Tax: $548 (2025)Community: On Top Of The WorldSpa: NoCondo
Taxes:$548
Remarks: Welcome home to your 2 bedroom 2 bath 1400 sq ft Emerald model on the WEST side of Top of the World with a view of the pool. This open concept floor plan has updated laminate and freshly painted. You will have plenty of storage with all the closets. Not only do you have Hurricane IMPACT Windows but also have hurricane shutters for extra protection. A/C Was replaced in 2019 and water heater was replaced in 2026. Don?t miss your chance to make this piece of paradise your own! Assigned parking. The 55+ community has two activity centers, and two private golf courses with 9 and 18 holes, free exclusively for resident 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. All washer, dryer and hookups must be approved by the association.
Listing Agent: Jason Johantgen (727-422-2352)
2076 BUTTERNUT CIR W, CLEARWATER, FL 33763
$370,000128 Days on yellowkey MLS ID: TB8473247
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1341 Built: 1980Community: Charter OaksSingle Family
Taxes:$0
Remarks: Price Improvement!! Great opportunity in Clearwater’s desirable Charter Oaks area! This comfortable home offers 2 bedrooms, 2 full baths, bonus room, in-ground pool, and a spacious fenced backyard — perfect for outdoor enjoyment or future upgrades. This could be a clean Slate for a Savy Home owner or Investor, alike. With updated electrical and newer roof, Just needs a cosmetic renovation. Located in a welcoming Clearwater community with easy access to shopping, dining, parks, and major roads just a short drive to Clearwater’s beaches and Dunedin’s luxury lifestyle. Being Sold As-Is, Where-Is; fewer contingencies preferred for offers. This is your chance to buy an investment home, In an amazing area with a Pool.
Listing is courtesy of: JAY ALAN REAL ESTATE (855-529-2526)
Listing Agent: Orlando Izquierdo Jr (727-692-5922)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.