Pinellas Homes with Trail(s) Amenities

Pinellas Homes with Trail(s) Amenities

Welcome to Pinellas County, Florida, a stunning coastal paradise that seamlessly blends vibrant urban life with the tranquility of nature. Nestled along the Gulf of Mexico, Pinellas is renowned for its beautiful beaches, charming communities, and a wealth of recreational opportunities. With cities like St. Petersburg and Clearwater, this county is not only a haven for sun-seekers but also a flourishing hub for culture, dining, and arts.

For those seeking a home that embraces the outdoors, Pinellas County offers a variety of properties equipped with exceptional trail amenities. Imagine stepping out of your front door and onto a scenic trail, where you can enjoy leisurely strolls, invigorating bike rides, or peaceful runs surrounded by lush landscapes. Many neighborhoods here prioritize outdoor living, featuring well-maintained paths that connect residents to parks, waterfronts, and nature preserves.

Whether you're looking for a charming single-family home, a modern condo, or a luxurious waterfront estate, you’ll find that homes with trail amenities in Pinellas County cater to an active lifestyle. These properties not only provide easy access to the natural beauty that the area is famous for, but they also foster a sense of community among outdoor enthusiasts.

With year-round sunshine, a friendly atmosphere, and endless opportunities for adventure, Pinellas County is the perfect place to call home. Embrace the Florida lifestyle and discover your dream home today, where trails and tranquility await just outside your door!

Newest Pinellas Homes with Trail(s) Amenities

1 Beds ⋅ 1 Baths ⋅ Waterside At Coquina Key South SubDv. ⋅ 33705 Zip Code

This 1 bedroom, 1 bath unit comes with a private boat slip! The boat slip is located behind Bldg. 60 on Canal #5, three building down from unit. Slip has electric and water along with a storage box. The unit has upgraded cabinets, granite countertops and sleek stainless-steel appliances, stack washer/dryer in kitchen closet. Private balcony provides views of the saltwater canal to enjoy while having your morning coffee or savoring a sunset cocktail. The Waterside South community has 24-hour gated entrance with on-site security and is PET FRIENDLY. This waterfront location allows you to stroll along 88 acres of lush, landscaped waterfront and 3 miles of sea paths along Tampa Bay. Enjoy cocktails and dinner at the exclusive, private two story Waterside Yacht Club, which offers full liquor sports bar, nightly specials in the restaurant and gorgeous water views. The Waterside community features two pools, one of which is right on the bay with a hot tub, and there is a fully equipped gym open 24/7. The clubhouse also has saunas, billiards room, library/game room, vending machines, ice machine and laundry facilities. This private yacht club has an elevator and may be booked for private events. Relax and do some fishing from the private Fishing Pier, play tennis under the lights, or opt for Pickleball, basketball, sand volleyball, horseshoes, or shuffleboard. Or take a stroll with your pooch at the on-site dog park with walking paths. Bicycle and Kayak racks are available for use. There are also Garages, Carports, Dry dock storage and Boat slips, accommodating boats up to 32’ , which are available for lease and additional purchase. Waterside South is a short commute from the bustling downtown and waterfront area of St Petersburg with its boutique shopping, dining, numerous museums, and many entertainment venues. Short drive to Fort DeSoto and the beautiful sands of St Petersburg Beach. Easy commute to Tampa and Tampa International Airport to the north and the iconic Skyway Bridge and Sarasota/Bradenton area to the south.

4728 Beach Drive Se Unit B, St Petersburg

3 Beds ⋅ 4 Baths ⋅ Bay Island Group 14 SubDv. ⋅ 33707 Zip Code

PENTHOUSE PARADISE! NO DAMAGE IN PRESIDENTIAL BUILDING FROM HURRICANES. This is a must see. SPECTACULAR 55+ waterfront living in the exclusive Bay Island 24 hour guard attended/gated community! This is an opportunity to own a penthouse unit in the Presidential building with wide open Gulf and Intercoastal water views that reach from Treasure Island to the Don Cesar on Pass-A-Grille.This HOA is on top of their game by completing the engineer reports and required repairs to satisfy state compliance, or state requirements . Enjoy watching sailboats, dolphins, manatees, and stingrays while soaking in those gorgeous gulf sunsets . This one-of-a kind unit was just remodeled from top to bottom. Roof was replaced 6 months ago. Interior remodeling includes: 17 sleek shaker doors, frames and brushed nickel hardware, all popcorn ceilings removed, elevated the ceilings in bathrooms, crown molding, can lighting replaced with recessed LED lighting, all non-carpeted floors changed to high end luxury vinyl and carpeting in all 3 bedrooms, 5 inch baseboards in every room, all new flat side toilets (4), 2 new AC units and handlers with google nest remote programmable thermostats, all duct work inspected, roof 1 year, new stainless steel appliances including: flat-top stove, microwave, large single sink, dishwasher, washer and dryer (2024), new kitchen island w/waterfall, 2 water heaters (2024), all floor to ceiling PGT hurricane windows throughout entire condo replaced, electronic shades, all new quartzite counters and backsplash in kitchen including new counter-height master bathroom vanity with quartzite counter 28ft of living room space feels like your sitting on the water . This unit is perfection from décor to stunning views. Bay Island Amenities include a marina, 5 pools, Jacuzzis, 4 tennis and pickle ball courts, outdoor grills with tikihut picnic areas, club house with ball room for rent, pool tables , Ping-Pong tables, dart board room ,card room, shuffle board court, saunas and showers, a his and hers fitness center with the updated equipment, a mile+ of waterfront sidewalks and a Social Director with multiple dances/community gatherings year round. In close proximity to restaurants, shopping, Sun Runner bus right at gated entrance. 2 front row covered parking spots near entrance with 2 elevator access.This HOA is on top of their game by completing the engineer reports and required repairs to satisfy state compliance, or state requirements . THIS IS A MUST VIEW.

7600 Sun Island Drive S Unit 804, South Pasadena

3 Beds ⋅ 3 Baths ⋅ Tara Cay Sound South SubDv. ⋅ 33776 Zip Code

Auction Property. ***Luxury Live Auction! *** Transparent Non-Distressed Auction! Saturday, August 15, 2026, at 11:00 am. Preview from 10:00 am on Sale Day. *** EVERYONE WELCOME TO BID *** Because this is an auction sale, the home may sell for less or more than the list price. The home is being sold free and clear of all debts and is guaranteed by title insurance, like any other traditionally listed home. *** You can use cash or financing.*** Experience waterfront resort-style living in the highly desirable Tara Cay community, surrounded by lush green spaces, manicured grounds, docks for your boat, a sparkling pool, and lounging areas. This spacious townhome offers nearly 2,000 square feet with 3 bedrooms, 3 full bathrooms, a bonus area, tranquil Intracoastal water views, and multiple outdoor living spaces overlooking the waterway. The main living level features a gourmet kitchen with a breakfast bar, dining area, and open living room designed to capture the peaceful resort-like setting. The kitchen was completely remodeled and updated in 2020, showcasing granite countertops, a custom tile backsplash, stainless steel appliances, generous cabinetry, and a walk-in pantry. Sliding doors lead to a private screened balcony, creating the perfect setting for morning coffee, outdoor dining, or relaxing as boats and wildlife pass by. Upstairs are two spacious primary suites, each with its own private bathroom and flexible sitting or office area. The larger waterfront suite features vaulted ceilings, two walk-in closets, a private screened balcony, and a beautifully updated en suite bathroom with granite finishes and a large tiled walk-in shower. The second suite provides excellent privacy for family members or overnight guests, complete with a full bathroom and additional sitting space. Custom decks and balconies extend from the ground floor, living area, and primary bedroom, providing three separate places to enjoy the water and surrounding tropical landscape. The waterway opens to the Intracoastal Waterway with convenient Gulf access, while boat docks are located right out your back lanai and are available for multi-day and night docking for your boat or everyday use. Additional highlights include a newer air-conditioning system installed in 2018, an oversized tandem garage with abundant storage, a large storage closet, real wood flooring throughout the home, flexible bonus space, and low monthly maintenance fees. The community pool is only steps from the home, yet the setting remains quiet, private, and peaceful. Tara Cay offers the carefree atmosphere of a waterfront retreat just minutes from Gulf beaches, boat ramps, parks, restaurants, shopping, schools, and local attractions. Whether enjoying the pool, launching a kayak, docking your boat, or unwinding on one of your private balconies, this exceptional townhome delivers the Florida waterfront lifestyle without the upkeep of a single-family waterfront property. ........BUYER will receive a general warranty deed free and clear of all debts, guaranteed with a title insurance policy at closing..... 4–Point Inspection Available *****Submit an acceptable contract to stop the auction!*****

9870 Indian Key Trail Unit 64, Seminole

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Welcome to this stunning corner-unit condo offering 2 bedrooms and 2 bathrooms, beautifully updated with luxury vinyl flooring throughout. Filled with natural light, this bright and inviting home features an open-concept kitchen that flows seamlessly into the living and dining areas, creating the perfect space for everyday living and entertaining. With approximately $47,000 in upgrades, this home has been thoughtfully enhanced for both style and peace of mind. The kitchen is equipped with stainless steel appliances installed in 2023, while updated hurricane-impact windows provide added security and energy efficiency. The water heater was replaced in 2025, and the primary bathroom has been tastefully renovated with modern finishes. The location is exceptional situated just steps from the clubhouse and pool, you'll enjoy easy access to community amenities. Relax from the comfort of your home with front-row views of clubhouse activities or simply walk over and join the fun. This move-in-ready residence combines modern updates, abundant natural light, and an unbeatable location.

2380 World Parkway Boulevard Unit 40, Clearwater

3 Beds ⋅ 2 Baths ⋅ Mariner Village Northwest Condo SubDv. ⋅ 34689 Zip Code

Penthouse Living on a Scenic Peninsula Surrounded by the Gulf, St. Joseph Sound and a Nature Preserve along Florida's Gulf Coast! Welcome to your own peaceful and private retreat—a beautifully updated, move-in ready 4th-floor penthouse condominium offering the perfect blend of luxury, tranquility, and coastal convenience. This spacious 3-bedroom, 2-bath residence is easily accessible via elevator and showcases breathtaking panoramic views overlooking a Protected Nature Preserve and Bird Sanctuary, with a peek of the sparkling Gulf beyond. Wake each morning to Spectacular Sunrises from your expansive private balcony, where coffee comes with a front-row seat to Florida's natural beauty. The unit has been fully renovated down to the cinder blocks with new electric, plumbing, impact rated sliders, insulated perimeter walls and ceilings, solid core doors, wood cabinetry porcelain tile, granite, etc., and all improvements were permitted and up to codes. Your condo fees include just about everything. You only pay electric (avg. $70/mo) and interior insurance. This exceptional community offers 24/7 gatehouse with controlled access, an unmatched waterfront lifestyle with resort amenities that include Pickleball, Tennis, Pool, Gym, Bocce Ball, Kayaking, Fishing and a Walking Trail along the water, plus year-round events and social activities. Enjoy peaceful walks, abundant wildlife, and the convenience of a Marina in complex, where boat slips are available for lease—making it easy to spend your days on the water. The location is second to none. You're just minutes from Sunset Beach and Howard Park Beach, Historic Downtown Tarpon Springs and the world-famous Sponge Docks, Downtown Dunedin named one of south’s “Best Beach Towns”, Gorgeous Honeymoon and Caladesi Islands, top rated Clearwater Beach and Innisbrook Golf & Country Club, home of the PGA TOUR's Valspar Championship. Whether you're looking for a full-time residence, seasonal getaway, or investment in one of Florida's most desirable coastal communities, this penthouse delivers an exceptional combination of comfort, views, and location. Don't let this one pass you by!

244 Mariner Drive Unit 244, Tarpon Springs

2 Beds ⋅ 2 Baths ⋅ Mariner Village Northwest Condo SubDv. ⋅ 34689 Zip Code

Welcome to PENTHOUSE LIVING on FLORIDA’S SPECTACULAR GULF COAST! This rarely available 2-bedroom, 2-bath penthouse condo offers an exceptional “Waterfront Lifestyle” on a secluded peninsula surrounded by the Gulf and St. Joseph Sound. Unwind every evening with unforgettable water views and colorful skies looking towards Sunset Beach, and wake up each morning to breathtaking sunrises over a protected nature preserve and bird sanctuary, all from your expansive 60-foot private balcony. With panoramic views of the Gulf and surrounding natural beauty, this home provides a peaceful retreat while remaining just minutes from some of Florida's most sought-after destinations. The unit has been fully renovated down to the cinder blocks with new electric, plumbing, impact rated sliders, insulated perimeter walls and ceilings, solid core doors, wood cabinetry porcelain tile, quartz counters, etc., and all improvements were permitted and up to codes. Your condo fees include just about everything. You only pay electric (avg. $60/mo) and interior insurance. Resort style amenities include Pickleball, Tennis, Pool, Gym, Bocce Ball, Kayaking, Fishing and a Walking Trail along the water. The community has year-round events and social activities. All State required condo inspections have been completed and passed, copies available upon request. Take the new elevator up to your penthouse. The building is concrete block and did not flood during recent storms. Gated community with gatehouse attendents 24/7. Located in the desirable Mariner Village Community, you're just around the corner from Sunset Beach and a short drive to the Award-Winning shores of Clearwater Beach, Honeymoon Island, and Caladesi Island. Enjoy the charm of historic downtown Tarpon Springs, famous for its Sponge Docks, authentic Greek restaurants, waterfront shopping, and year-round festivals, or spend the day exploring nearby downtown Dunedin, one of Florida's favorite coastal towns. Golf enthusiasts will appreciate the close proximity to the renowned Innisbrook Golf Resort, home of the PGA TOUR's Valspar Championship. For those who love life on the water, walk over to Tarpon Cove Marina where you can lease a boat slip. The Marina provides deep water access to the Gulf with NO Bridges, making it easy to enjoy boating, fishing, and sunset cruises. Whether you're relaxing on the balcony, watching dolphins and coastal wildlife, entertaining friends with spectacular waterfront views, or simply enjoying the serenity of this unique Gulf-front setting, this penthouse offers an extraordinary combination of luxury, privacy, and convenience. Opportunities to own a penthouse with this level of panoramic scenery, expansive outdoor living space, and unbeatable location are exceptionally rare, making this an ideal primary residence, seasonal getaway, or investment in one of Florida's most desirable coastal communities.

243 Mariner Drive Unit 243, Tarpon Springs

2 Beds ⋅ 1 Baths ⋅ Woodlake 1 Condo SubDv. ⋅ 33765 Zip Code

Welcome home to this well-maintained 2-bedroom, 1-bath condominium in the established Woodlake community, where pride of ownership shines through after being lovingly cared for by the same family for more than 40 years. Offering a clean, functional layout and durable tile flooring throughout, this residence is ready for its next chapter. Enjoy peace of mind with several important updates already completed, including a new HVAC system (March 2026), refrigerator, dishwasher, microwave, and washing machine (2024), toilet (2023), electrical panel (2009), and tub surround (2009). Woodlake offers residents beautifully maintained grounds along with amenities that include a community pool, tennis courts, clubhouse, and recreational areas. The community is centrally located in Clearwater, providing convenient access to shopping, dining, parks, medical facilities, Downtown Dunedin, Safety Harbor, Tampa International Airport, and the world-famous Gulf beaches. Whether you're searching for a primary residence, seasonal getaway, or low-maintenance Florida lifestyle, this home offers an excellent opportunity in one of Clearwater's well-established condominium communities.

2054 Sunset Point Road Unit 38, Clearwater

2 Beds ⋅ 1 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Virtually Staged. Move-In Ready 2-Bedroom Condo in Desirable On Top of the World! Welcome home to this bright and inviting 2-bedroom, 1-bath condominium in Clearwater's sought-after On Top of the World 55+ community. Offering approximately 1,100 square feet of comfortable living space, this well-maintained residence is vacant and move-in ready, making it an excellent opportunity for year-round living or a seasonal Florida retreat. The thoughtful floor plan features spacious living and dining areas, generous bedroom sizes, and the convenience of both front and rear entrances. Window coverings are included, allowing you to settle in immediately and add your own personal touches over time. Residents of On Top of the World enjoy an active, resort-style lifestyle with an impressive array of amenities. The community offers multiple swimming pools, fitness facilities, tennis and pickleball courts, shuffleboard, lawn bowling, hobby studios, a woodworking shop, billiards, card rooms, library, and numerous clubs and social activities. Golf enthusiasts will appreciate access to the community's golf courses, while pet owners can enjoy the on-site dog park. Beautiful walking paths, scenic ponds, and mature landscaping create a peaceful setting throughout the neighborhood. Ideally located, you'll be just minutes from Clearwater's award-winning Gulf beaches, shopping, dining, medical facilities, cultural attractions, and both Tampa International and St. Pete-Clearwater International airports. The monthly HOA fee of $500.23 provides exceptional value and includes a wide range of community amenities, helping you enjoy a carefree Florida lifestyle. Whether you're looking for a full-time residence or a winter getaway, this inviting home offers comfort, convenience, and the vibrant lifestyle that has made On Top of the World one of Clearwater's most popular active adult communities.

2451 Canadian Way Unit 29, Clearwater

2 Beds ⋅ 2 Baths ⋅ On Top Of The World SubDv. ⋅ 33763 Zip Code

Looking for one of the BEST VALUES in On Top of the World? This BEAUTIFULLY UPDATED 2-BEDROOM, 2-BATH condo offers approximately 1,400 square feet in one of Clearwater's premier 55+ communities. Perfectly positioned DIRECTLY ACROSS FROM THE GOLF COURSE, this third-floor residence enjoys ONE OF THE MOST PRIVATE AND SERENE REAR VIEWS IN ON TOP OF THE WORLD, overlooking a semi-wooded setting with mature trees that provide exceptional privacy and a peaceful backdrop. PET FRIENDLY with NO WEIGHT OR NUMBER RESTRICTIONS for dogs, a rare feature among 55+ communities. Inside you'll find UPDATED TRAVERTINE AND PREMIUM STRAND-WOVEN BAMBOO FLOORING, an UPDATED KITCHEN featuring QUARTZ COUNTERTOPS, modern appliances, and a thoughtfully designed pantry cabinet that keeps the microwave at convenient counter height while preserving valuable countertop space. UPDATED BATHROOMS include a renovated guest bath with a comfort-height commode, and the home also offers the convenience of an IN-UNIT WASHER & DRYER. For added peace of mind, Seller will pay for a HOMEOWNER'S WARRANTY. The $535 monthly condo fee includes WATER, SEWER, TRASH, HIGH-SPEED FIBER OPTIC INTERNET, 120 BASIC CABLE CHANNELS, BUILDING INSURANCE, exterior maintenance, and maintenance of the community's outstanding amenities, including UNLIMITED GOLF on both the 9-hole and 18-hole golf courses at no additional cost. Residents enjoy two heated pools, tennis, pickleball, a remodeled fitness center and cardio gym, hobby studios, a woodshop, library, dog park, fishing, kayaking, daily shuttle service, Good Karma Café, and an active calendar of clubs, classes, and entertainment. Conveniently located just minutes from Clearwater Beach, downtown Dunedin, shopping, dining, and medical facilities, this exceptional home offers the perfect opportunity to enjoy Florida's active adult lifestyle in one of Clearwater's most desirable 55+ communities.

2430 Florentine Way Unit 56, Clearwater

1 Beds ⋅ 1 Baths ⋅ Long Bayou SubDv. ⋅ 33708 Zip Code

Well-maintained GROUND FLOOR 1 bedrioom1 bath has a sunny Bonus room, suitable as an office or guest bedroom which includes a cabinet-style queen size Murphy bed (with storage and USB/Electrical portals,) and a walk-in storage closet. The Bedroom also has a walk-in closet, and a new ceiling fan with remote. The high-ceiling Kitchen has stainless appliances, gas stove, over-the-sink lighting, and a separate large Pantry cupboard, along with generous white cabinets. The Bathroom has granite counters, new shower head with wand, and a linen cabinet. Newly painted throughout, the spacious living/dining room has a ceiling fan/light with wall control. The Unit has large neutral ceramic tile throughout, a new electrical panel (2025) that complies with new Code, a new roof (2026), A/C (2021) with a 10-year warranty and new condenser fan (2026) , Upgraded windows (2021), and Hurricane shutters for the Bonus room window. Covered private parking and visitor parking is directly in front of the bonus room entry. Owner has paid all Special Assessment installments for 2026, and the low HOA fees include everything except electricity and phone. Long Bayou offers every amenity for a vibrant active social lifestyle: heated pool, hot tub, pickleball, tennis, clubs and activity groups, an auditorium for special events etc. all in lush and well-kept grounds and walking trails throughout the gated complex.

10034 64th Avenue N Unit 11, St Petersburg

1 Beds ⋅ 2 Baths ⋅ Seapointe Terrace Condo SubDv. ⋅ 33711 Zip Code

Wake up to breathtaking, unobstructed Tampa Bay views, spectacular sunrises, playful dolphins, and the waterfront lifestyle you’ve been dreaming of. From the moment you step inside, your eyes are drawn through the residence to the expansive waters of Tampa Bay beyond. Thoughtfully designed, this beautifully updated 1-bedroom, 2-bath condominium maximizes its 890 square feet with an open layout, two private patios, and water views from both the living room and the primary bedroom. Hurricane-impact sliding glass doors open to a covered waterfront patio with unobstructed Tampa Bay views, while a second set of impact sliders off the kitchen leads to a private front patio, creating inviting outdoor living on both sides of the home. Recent updates include remodeled bathrooms, new cabinetry, new appliances, an upgraded electrical panel, newer HVAC, and a convenient laundry closet in the second bath. Located in highly desirable Seapointe Terrace, this residence features one of the lowest HOA fees in the community at just $788 monthly. The HOA includes insurance, water, sewer, trash, cable, high-speed internet, building reserves, and resort-style amenities including a heated waterfront pool, tennis and pickleball courts, a fishing pier, kayak launch, kayak and bike storage, and additional community storage. The milestone inspection has been completed, and the association has fully funded reserves, offering added peace of mind. Ideally located with quick access to I-275, downtown St. Petersburg, Fort De Soto Park, and the Gulf beaches, you’re also just a short walk to the newly popular SkyBeach Resort, the marina, and waterfront dining. Whether you’re searching for a full-time residence or the perfect Florida retreat, this move-in-ready waterfront home offers exceptional updates, outstanding amenities, and an unbeatable Tampa Bay location.

7530 Sunshine Skyway Lane S Unit T30, St Petersburg

4 Beds ⋅ 4 Baths ⋅ Tara Cay Sound North SubDv. ⋅ 33776 Zip Code

Find your slice of Florida paradise in one of the Seminoles favorite waterfront communities, Tara Cay Sound. Perfectly positioned along the intracoastal waterway with several community boat docks for boating, kayaking, paddle board & fishing for year round outdoor activities. Located in the North village where it's highly elevated and has never flooded! So just pack your bags and move right in to this already fully furnished home! You will love this 3-story townhouse with 2 spacious primary suites! One primary offers an en suite bath, double closets with an added bonus space to make as you choose; an office, exercise area, or cozy retreat. The 2nd primary suite offers 2 walk in closets with a private balcony and spa inspired bathroom featuring a garden/spa tub, dual sinks & separate walk in shower. The heart of the home is on the 2nd floor featuring an open-concept floor plan with durable light & bright ceramic tile throughout. Here, you find the 3rd bedroom, bath, and kitchen that offers a breakfast bar overlooking the dining & living areas with nice, bright outdoor views from the patio, creating the perfect space for family time & entertaining. The 4th bedroom on the 1st floor is best for the family member, in-law, or guest who wants their own space & privacy, equipped with a kitchenette, bathroom & enclosed patio plus private entry from the garage. NEW ROOF 2024, NEW WATER HEATER 2025, added water softener are a few good updates. PET FRIENDLY, LOW HOA just $417 a month and covers maintenance grounds, reserves, community pool, cable, internet, trash, water & sewer. TOP RATED SCHOOL DISTRICT! Come find your new & furnished coastal retreat right here!

14883 Seminole Trail Unit 130, Seminole

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