Active Adult 55+ Homes for Sale in Clearwater, FL

2 Beds ⋅ 2 Baths ⋅ Village On The Green SubDv.

Welcome to 2506 Oakleaf Lane #B, a bright, open and spacious villa nestled in the desirable community of Village On The Green in Clearwater. This inviting home offers a comfortable, easy-living floor plan with plenty of natural light. The open kitchen features a convenient pass-through to the great room area, creating an ideal flow for entertaining and everyday living. The spacious living area opens to a wonderful enclosed porch, providing an additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The gorgeous primary bathroom is a standout feature, offering a beautiful walk-in shower and a comfortable, updated feel. Additional highlights include newer windows, a newer electrical panel, and a convenient inside laundry room. Outside, you'll appreciate the assigned covered carport parking located close to the home, along with a private outdoor storage space for added convenience. Village On The Green offers a wonderful community lifestyle with an active clubhouse featuring social and recreational spaces, along with a solar heated pool, library, kitchen, gathering room and card room. The community is conveniently located near shopping, dining, downtown Dunedin and the beautiful Gulf beaches. Light, spacious, comfortable and well located, this charming villa offers the opportunity to enjoy the best of the Village On The Green lifestyle! Located in a NON FLOOD ZONE!

2506 Oakleaf Lane Unit 25B, Clearwater

$209,900

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv.

This beautiful and pristine condo has been renovated from top to bottom. It is in a 55+ community, has 2-bedrooms, 2-bathrooms and is on the second-floor with an elevator. Brand new AC in 2025. The pet friendly neighborhood is ready to welcome you home! Thoughtfully refreshed throughout, the unit features fresh paint, an updated kitchen with quartz countertops and newer appliances, and beautifully updated bathrooms. A versatile bonus room just off the kitchen offers endless possibilities, use it as a dining area, TV room, home office, or additional guest space. Partial furnishings are also available, making your move even easier. Enjoy an unbeatable location close to Gulf beaches, airports, medical facilities, shopping, dining, entertainment, and everything you need for an easy Florida lifestyle. The community offers an impressive array of amenities and activities, including two heated pools, a dog park, fitness center, two golf courses, card games, many clubs, dancing, social events and plenty of opportunities to meet new friends and stay active. Whether you're looking for a full-time residence, seasonal getaway, or a place to enjoy the best of Florida living, this move-in-ready condo is a must-see. Schedule your private tour today and make this wonderful home yours!

2256 Spanish Drive Unit 42, Clearwater

$150,000

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv.

Tucked into the sought-after On Top of the World 55+ community, this well-maintained 2-bedroom, 2-bath residence offers 1,100 square feet of comfortable living space with a layout that feels open, functional, and easy to enjoy. The spacious living and dining areas flow naturally together, creating plenty of room for quiet evenings at home or gathering with friends and family. The kitchen offers abundant cabinetry, generous counter space, a ceiling fan, and a dedicated eat-in area for casual meals or morning coffee. The primary suite provides a private place to unwind, complete with ample closet space and an en suite bath. A second bedroom and full bath offer flexibility for overnight guests, a home office, hobby space, or whatever best fits your lifestyle. One of the home's standout features is the enclosed Florida room, adding valuable extra space that can be enjoyed throughout the year. Use it as a reading room, sitting area, game room, craft space, or simply a comfortable spot to relax and enjoy the Florida lifestyle. Living in On Top of the World means more than just having a place to call home. Residents enjoy an active, resort-style community with golf, swimming pools, fitness facilities, walking areas, clubhouses, social clubs, activities, and recreation designed for a wide range of interests. Whether you're looking for a full-time residence, seasonal escape, or an easy-to-maintain home in an established 55+ community, 2370 Jamaican Street, Unit 30 offers a comfortable setting, versatile living space, and access to one of the area's most popular active-adult lifestyles.

2370 Jamaican Street Unit 30, Clearwater

$119,900

1 Beds ⋅ 1 Baths ⋅ Marilyn Pines Condo Apts SubDv.

Welcome to Marilyn Pines, a peaceful 55+ community tucked away on a dead end street, yet perfectly located in the heart of Clearwater. This condo is a first floor unit and an end unit in one of the community's few detached single level buildings, highly sought after for added privacy and convenience. An inviting front porch greets you, perfect for morning coffee and relaxing. As you enter the unit, the kitchen provides ample room to function and a spacious dining and living room combo flows into a back sun room with plentiful natural light and sliders (updated hurricane impact - along with windows) that open to additional outdoor space out back. The bedroom is nicely sized and also features slider access to the sun room as well as a walk in closet. a community pool , clubhouse and other features are also included. Location is truly ideal, minutes away from golf, shopping, restaurants, Clearwater Beach, spring training baseball and more..

2060 Marilyn Street Unit 118, Clearwater

$99,000

2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv.

Discover the easygoing Florida lifestyle at On Top of the World! This spacious 2 bed, 1bath, 1,100 sq. ft. condo is located on the 3rd floor as an interior end unit in one of Clearwater’s most active and amenity-rich 55+ communities. The comfortable layout features abundant closet space and storage, including wall-to-wall closets in the primary bedroom. A versatile bonus room off the back adds valuable flex space for a second living room, home office, den, study, hobby room or workout area. Lovingly cared for and successfully rented seasonally for nearly 20 years, the condo makes an appealing Florida getaway or full-time or seasonal residence. The interior retains its original character, offering a blank canvas for a new owner to update and personalize to their own taste. The home is offered fully furnished, with the option to have the furnishings removed before closing if desired. An elevator, assigned parking space and dedicated storage space just outside the unit add everyday convenience. Beyond your front door, OTOW offers an incredible array of amenities and activities, including more than 175 clubs, 2 swimming pools, 4 tennis courts, pickleball, a fitness center, dog park, horseshoe pits, lawn bowling and shuffleboard. Approved resident owners with a valid Activity Card also enjoy FREE golf on the community’s 2 courses—an exceptional perk for golf enthusiasts! With a vibrant social atmosphere, pet-friendly environment and something for everyone, On Top of the World makes it easy to stay active, connected and entertained. All this, just minutes from Clearwater’s beautiful beaches, shopping, dining, medical facilities and more. Come see what makes OTOW such a special place to call home!

2455 Finlandia Lane Unit 63, Clearwater

$179,900

2 Beds ⋅ 2 Baths ⋅ Sunshine Terrace Condo SubDv.

Just completly renovated, ground floor, end unit that is drop dead geourgeous, features 2 bedroom, 2 bath, unit with direct access infront of unit carport parking. All new stainless appliances, kitchen cabinets and solid surface counter tops. This just completed renovation also includeds both bathrooms, tankless hot water heater, plus a stakable washer / dryer in hall bathroom. The rooms are spacious, plenty of storage space, and the windows were also recently replaced. Fantastic smaller condo community also has a awesome pool area and clubhouse that is located in the heart of Clearwater, and close to everthing. This is a well cared for and extremely nice ground floor, end unit that is hard to come by.

1239 S Martin Luther King Jr Avenue Unit 104, Clearwater

$109,000

1 Beds ⋅ 1 Baths ⋅ Woodland Villas Condo 1 SubDv.

Welcome to this beautifully refreshed Clearwater condo offering comfortable, low-maintenance living in a convenient location. This move-in-ready unit features a freshly painted interior, creating a clean, bright, and inviting atmosphere throughout. The kitchen is equipped with stainless steel appliances and provides a functional space for everyday cooking and entertaining. Major mechanical updates provide added peace of mind, including an HVAC system replaced in 2022 and a water heater replaced in 2025. Whether you're looking for a primary residence, second home, or investment property, this well-maintained condo is a great opportunity. Don't miss your chance to make this your new home! ***Cannot accept FHA until 11/04/2026***

2465 Northside Drive Unit 1604, Clearwater

$88,800

1 Beds ⋅ 1 Baths ⋅ Drew Ridge Apts Co-Op SubDv.

1BR/1BA Condo in Clearwater 55+ Community – $90,000, Tenant-Occupied at $1,300/mo This 1-bedroom, 1-bath, 705 sq ft unit in a well-established Clearwater 55+ community is currently leased at $1,300/month with no known issues, no deferred maintenance, and no special assessments. The tenant is on a 12-month lease and has no intention of leaving, so this works as an income property from closing. If you're buying to occupy it yourself, the lease includes a 4-month move-out clause, so you're not locked in long-term either way. HOA is $450/mo. Close to shopping, dining, medical facilities, and major roadways. Sellers are motivated. Schedule a showing today.

1221 Drew Street Unit B3, Clearwater

$139,900

2 Beds ⋅ 2 Baths ⋅ Marilyn Pines Condo Apts SubDv.

JUST BRING YOUR TOOTHBRUSH! Whether you're searching for a full-time Florida home, seasonal getaway, or investment opportunity, this fully furnished 2-bedroom, 2-bath condo in a desirable 55+ Clearwater community is ready for you to move right in! Located on the second floor, this spacious condo offers a fantastic view overlooking the community pool, sauna, clubhouse, and shuffleboard courts. The open and comfortable floor plan provides plenty of space for everyday living and entertaining, with two generously sized bedrooms and two full bathrooms. Start your morning with coffee overlooking the peaceful pool area, or relax at the end of the day while enjoying the wooded tree views from the front. The kitchen features an updated countertop and sink, adding a fresh touch to the home.One of the biggest perks is the competitive monthly maintenance fee, which includes water, sewer, trash, cable, internet, and more! And when it's time for fun in the sun, you're just a short drive from beautiful Clearwater Beach and all the shopping, dining, entertainment, and attractions that make the Tampa Bay area such a desirable place to live. Fully furnished. Great location. Fantastic amenities. Move-in ready. Come see why this Clearwater condo could be the perfect place to call your Florida home! Maintenance is very competitive an includes Water, Sewer, Trash, Cable , Internet and More! Just a short drive to beautiful Clearwater Beach and everything the Tampa Bay area has to offer.

2060 Marilyn Street Unit 209, Clearwater

$185,900

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv.

Virtually Staged. Welcome home to carefree Florida living in On Top of the World Clearwater, one of Florida’s most desirable 55+ golf communities. Located at 2285 Israeli Drive, #57, this spacious 2-bedroom, 2-bath third-floor condo offers approximately 1,400 sq ft of comfortable living designed for easy enjoyment and relaxation. The kitchen features upgraded cabinetry, countertops, and backsplash, creating a stylish and functional space for everyday living or entertaining. The generous primary suite includes a spacious closet and private bath with shower, along with the convenience of an in-unit stackable washer and dryer. The guest bedroom sits adjacent to a full hall bath with tub — perfect for visitors or an ideal home office setup. Start your day with coffee or unwind in the enclosed Florida room overlooking peaceful, landscaped grounds — a perfect extension of your living space. Recent updates provide peace of mind and modern appeal, including a refrigerator, dishwasher, HVAC system, double-pane windows, updated lighting, new toilets, refreshed bathroom cabinetry and countertops, recessed lighting in the kitchen and Florida room, and attractive vinyl flooring throughout (no carpet). Residents enjoy an exceptional resort-style lifestyle with world-class amenities, including two activity centers, two private golf courses (9-hole and 18-hole) free exclusively to owners, two heated pools, a remodeled cardio gym, hobby studios, wood-working shop, and a fenced dog park with covered seating. Social opportunities abound with fitness classes, clubs, dancing, cards, billiards, entertainment, and more. The on-site Good Karma Café offers convenient take-and-bake meals and snacks. Your monthly condo fee (approximately $565) covers water, sewer, trash, cable, internet, exterior maintenance, and full access to recreational facilities — delivering truly maintenance-free living. Ideally located just minutes from Clearwater Beach, the Dunedin Causeway, shopping, dining, medical centers, and transportation, this home offers the perfect blend of convenience, community, and coastal lifestyle. Whether you’re downsizing, searching for a seasonal getaway, or planning for long-term living, this move-in-ready residence is a wonderful opportunity to enjoy the best of Florida living. Note: Property is conveyed by leasehold estate deed. Association approval required. If financing, a minimum 35% down payment is required.

2285 Israeli Drive Unit 57, Clearwater

$235,000

2 Beds ⋅ 2 Baths ⋅ Lakes Unit I The SubDv.

Nice price reduction on an already competitively priced home. Welcome to The Lakes a 55 + well kept community. Lots of opportunity here with this 2 bed 2 bath 1 car garage with 2 spacious living areas laminate flooring through out. Newer roof & hurricane impact windows. Pool is located just across the street so very easy access. Good bones here so put this on your must see, priced fairly and will sell quickly. Low maintenance fees with good reserves. Shopping/Beaches/ Restaurants/Medical & I-275 all close by and so convenient. Put this on your must see list immediately INVESTORS PUT THIS ON YOUR LIST Bring us a reasonable offer

4476 Lake Boulevard, Clearwater

$189,900

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv.

Welcome to this spacious 2-bedroom, 2-bathroom, 1400 sq ft condo, conveniently located next to the East community center, walking distance from pools, tennis courts, pickle ball and golf courses. This tastefully updated condo has it all. Featuring updated luxury vinyl flooring and paint throughout. Living room/ Dining room combo. Updated impact windows. Updated kitchen featuring granite countertops, tile back splash, updated Stainless Steel Refrigerator, Dishwasher, Microwave and Garbage Disposal. Added pantry for plenty of storage. The master bedroom has an updated en-suite bathroom featuring, updated vanity, tile and toilet. The A/C was replaced in 2019. Furniture is optional. Make a 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.

2401 Ecuadorian Way Unit 57, Clearwater

Active Adult 55+ Homes for Sale in Clearwater, FL

All Active Adult 55+ Homes for Sale in Clearwater, FL

Joseph Sullivan Real Estate

Search

Resources

About