Clearwater Homes with Private Entrance Exterior Features

Clearwater Homes with Private Entrance Exterior Features

Welcome to Clearwater, Florida—a vibrant coastal gem nestled in Pinellas County. Known for its stunning white-sand beaches, Clearwater offers a perfect blend of relaxation and adventure. With its picturesque waterfront, charming downtown, and a plethora of recreational activities, it’s no wonder that Clearwater has become a sought-after destination for homebuyers and vacationers alike.

Imagine stepping out of your private entrance, greeted by the gentle sea breeze and the sound of waves lapping against the shore. Homes in Clearwater with private entrance exterior features offer a unique sense of privacy and exclusivity, making them ideal for those who value their space. These residences often come with beautifully landscaped yards, inviting patios, and outdoor living areas that beckon you to unwind and soak in the Florida sunshine.

In Clearwater, you can enjoy a plethora of outdoor activities, from kayaking in the crystal-clear waters to exploring the scenic trails of Caladesi Island State Park. The vibrant local culture is reflected in its eclectic dining scene, lively festivals, and art galleries. Whether you're strolling along the famous Pier 60 or savoring fresh seafood at a waterfront restaurant, Clearwater’s charm is undeniable.

Whether you’re looking for a year-round residence or a vacation retreat, Clearwater’s homes with private entrances provide the perfect sanctuary to enjoy the beauty and excitement of Florida living. Come discover your own slice of paradise in Clearwater, where the sun shines bright and the lifestyle is simply unmatched!

Newest Clearwater Homes with Private Entrance Exterior Features

$160,000
2 Beds ⋅ 2 Baths ⋅ Winding Creek Condominiums SubDv. ⋅ 33761 Zip Code
Discover this delightful corner unit condo featuring a fully furnished featuring two bedrooms and two bathrooms. This condo is nestled in the serene countryside area of Clearwater. Ideally situated amidst a vibrant array of restaurants, shopping mall, theatre, grocery stores and so close to the beach. Step inside to find a bright and inviting interior complete with dining area and a large living room. There is also an enclosed lanai area that can easily serve as a workspace or cozy bonus area. Also, this unit has a full size washer and dryer adding to the convenience of living here. The community amenities are sure to impress with a large heated pool, hot tub and enjoy playing pickleball with your friends while cooking out on the barbecue grills and picnic area next to the pool. All of this is just minutes from the Honeymoon State Park and renowed beaches surrounding this area. Don't miss out on this incredible opportunity. Come see your Florida home today!

2400 Winding Creek Boulevard Unit 18A-110, Clearwater
$489,000
3 Beds ⋅ 2 Baths ⋅ Longbrooke Sub Unit Two SubDv. ⋅ 33760 Zip Code
Welcome to your RENOVATED WATERFRONT home in the HIGHLY-DESIRABLE Longbrooke subdivision in Clearwater! This home, which has NOT flooded in any of the recent storms, has a beautiful BRAND NEW DECK overlooking Long Branch Creek. The creek leads out to Tampa Bay, meaning you could kayak or paddleboard out to the bay and enjoy the stunning views in the spacious water! Your mind will be at ease knowing the ROOF is only four years old (2022) and the HVAC is less than a year old (2025). This renovation was completed with both style and functionality in mind. The house has been FRESHLY PAINTED, inside and out, and updated with NEW LUXURY VINYL FLOORING. The kitchen is fully equipped with BRAND NEW APPLIANCES and QUARTZ COUNTERTOPS. The DOUBLE-SIDED WOOD BURNING FIREPLACE adds an extra layer of charm and the VAULTED CEILINGS open up the entire living space. Unwind in the completely UPDATED BATHROOMS that feature both bathtubs and walk-in showers, the best of both worlds. The entire home is brought together with BRAND NEW fans, fixtures, and blinds. The SCREENED-IN PORCH is perfect for you to relax as the sun goes down. The exterior has been THOUGHTFULLY LANDSCAPED and the protected woodlands in the backyard add a special touch of privacy. Don’t wait to jump on this opportunity, schedule a showing and come see it today!

3010 Longbrooke Way, Clearwater
$450,000
2 Beds ⋅ 3 Baths ⋅ Bayshore Twnhs SubDv. ⋅ 33759 Zip Code
Live the Florida you pictured. Tucked in a private enclave of 68 residences between Old Tampa Bay and downtown Safety Harbor, this three-story townhome frames a mangrove view from every level. Sip coffee on a screened balcony over the greenery, then hit the Bayshore Trail, linking the Ream Wilson and Courtney Campbell trails, for rides and paddleboarding. The middle level's open-concept kitchen, dining, and living add a workspace nook, half bath, and screened balcony over the mangroves. Above, a retreat under soaring ceilings offers a primary suite with private bath and screened balcony, a second bedroom, full bath, flexible office, and laundry. Below sits an oversized 4 car tandem garage and a screened lanai to a manicured lawn. Minutes to Safety Harbor's waterfront and dining; Tampa via the Courtney Campbell Causeway, St. Pete south, two airports close by. A carefree HOA covers roof, paint, landscaping, irrigation, termites, roads, pool, and entrances, with fire sprinklers on every floor.

38 Seagrape Circle, Clearwater
$271,225
3 Beds ⋅ 2 Baths ⋅ Winding Wood Condo Iii SubDv. ⋅ 33761 Zip Code
Virtually Staged. Experience refined Florida living in this beautifully updated 3-bedroom, 2-bath residence nestled in the popular Countryside area of Clearwater. Immaculate and move-in ready, this home showcases a tastefully remodeled kitchen featuring rich granite countertops, stainless steel appliances, and an elegant decorative range hood that anchors the space with sophistication. A separate den/office/family room adds an additional 300 heated square feet of flexible living space. New AC and patio roof recoated/sealed in 2024. Custom closet in primary bedroom and luxury vinyl plank flooring installed in 2025. New water heater just this month. Enjoy the ease of maintenance-free living with HOA services that include professional landscaping, exterior painting, roof maintenance, grounds care, and pest control. The heated community pool offers a serene escape, while the quiet cul-de-sac setting provides a rare blend of both privacy and tranquility. Ideally located near world-renowned Gulf beaches, premier shopping and dining, top medical facilities, public schools, cultural attractions and Tampa International Airport, this exceptional home delivers both luxury and convenience in one of Clearwater’s most desirable enclaves. Welcome Home!

2737 Haverhill Court, Clearwater
$438,500
3 Beds ⋅ 2 Baths ⋅ Clearview Heights SubDv. ⋅ 33756 Zip Code
Step inside and discover a home that blends thoughtful updates with comfortable everyday living. This beautifully maintained three bedroom, two bath home with an attached two car garage welcomes you with an open floor plan and attractive laminate flooring that flows throughout the living spaces. The heart of the home is the updated kitchen featuring custom designed cabinetry, quartz countertops, stainless steel appliances and LED recessed lighting that extends through the kitchen, living, and dining areas, creating a bright and inviting atmosphere. Both bathrooms have been tastefully remodeled with tile floors and quality finishes, while updated windows enhance energy efficiency and plenty of natural light. A brand new shingle roof has just been installed, providing added value and peace of mind. The spacious rear enclosed patio offers additional flexible living space, perfect for relaxing, entertaining or enjoying your morning coffee. Conveniently located near shopping, restaurants and schools with the Gulf Beaches just a short drive away. Come and see this amazing home today and make it yours tomorrow!

1628 S Highland Avenue, Clearwater
$2,200,000
4 Beds ⋅ 5 Baths ⋅ Overbrook Park SubDv. ⋅ 33756 Zip Code
Located in one of Belleair's most desirable neighborhoods, this remarkable residence offers a rare combination of luxury, flexibility, and peace of mind. More than a renovated home, it is a thoughtfully designed retreat created for generations to gather, celebrate, and create lasting memories. Tucked away at the end of a quiet road on a beautifully landscaped .39-acre homesite in the Town of Belleair, this exceptional residence welcomes you with a gracious brick paver circular driveway and brick paver entry, creating a striking first impression from the moment you arrive. Spanning 3,679 heated square feet, this extraordinary home has been completely reimagined with a perfect balance of timeless design, modern comfort, and exceptional functionality. Offering 4/5 bedrooms, 4 ensuite retreats (4.5 baths total) and thoughtfully designed for multigenerational living, the floor plan delivers a rare level of flexibility seldom found in today's market. Whether accommodating extended family, long-term guests, or creating private spaces for work and relaxation, each ensuite provides comfort, privacy, and independence while remaining connected to the heart of the home. The beautifully renovated interior showcases an inviting open flow with luxury vinyl flooring throughout, a stunning chef's kitchen featuring premium Café appliances, and refined finishes that create a sophisticated yet comfortable atmosphere. Just beyond the main living spaces, a dedicated wine and coffee bar room creates the perfect destination for entertaining and everyday enjoyment, complete with a large wine refrigerator and a full-size refrigerator with an ice maker. Each bathroom has been meticulously renovated with thoughtful details and quality craftsmanship, offering spa-like retreats throughout the home. A versatile second-level flex space further enhances the home's multigenerational appeal, offering endless possibilities as an in-law suite, guest quarters, private home office, media room, or recreation space. Complete with a kitchenette, private full bathroom with a walk-in shower, and a dedicated 2026 mini-split air conditioning system, it provides exceptional comfort and independence. The extensive transformation extends far beyond the visible finishes. Nearly every major component has been thoughtfully updated, including newer roof (2019 / 2024), hurricane-impact windows and doors, two high-efficiency HVAC systems (2023 and 2024) with whole-home air purification, three updated electrical panels, new insulation, updated lighting, ceiling fans, and countless additional improvements. The oversized two-car garage continues the home's exceptional attention to detail with a brick paver approach, epoxy flooring, and an energy-efficient 80-gallon hybrid heat pump water heater (2025) that also helps cool the insulated garage, creating a comfortable and versatile space. The outdoor living spaces provide a private sanctuary surrounded by exceptional landscaping and mature greenery. The beautifully resurfaced Pebble Sheen pool, complemented by new waterline tile and upgraded pool equipment, creates the perfect backdrop for relaxing afternoons, entertaining guests, and enjoying the Florida lifestyle year-round. Enjoy the video for a full tour of this amazing home.

411 Roebling Road S, Belleair
$450,000
3 Beds ⋅ 3 Baths ⋅ Skycrest Unit Ten SubDv. ⋅ 33765 Zip Code
Water Views... Peaceful Pond Setting... No Rear Neighbors! Enjoy tranquil pond views from the expansive covered front porch of this solid block Clearwater residence, ideally situated in a non-flood zone with no HOA. Offering 3 bedrooms, 3 full bathrooms, and an oversized 2-car garage, this home combines timeless character with thoughtful updates in a peaceful setting. Inside, you'll find two spacious living areas, including a bright, open gathering space and a cozy family room highlighted by a wood-burning fireplace—perfect for relaxing or entertaining. Beautiful terrazzo flooring flows throughout much of the home, preserving its authentic Florida charm, while solid 3-panel interior doors, recessed lighting, and no popcorn ceilings provide tasteful modern updates. The kitchen is equipped with a newer GE Profile stainless appliance package, offering both style and functionality for everyday living. The generously sized primary suite features a versatile sitting area that is ideal for a home office, reading nook, or private retreat and offers direct access to the outdoor living space. The newly renovated en suite bathroom has been thoughtfully designed with quality finishes. The secondary bedrooms are spacious and share a beautifully renovated guest bathroom complete with a double-sink vanity and a tub/shower combination. Additional improvements include hurricane-impact windows, a hurricane-rated garage door, a brick-paver driveway, a brick-paver rear patio, a fenced backyard, and a whole-house water filtration system. Major updates include a 2022 A/C system, 2018 roof and 2026 water heater, providing peace of mind for years to come. Conveniently located just minutes from The Sound, Clearwater's premier open-air waterfront amphitheater, where you can enjoy concerts, festivals, and community events. You'll also appreciate being a short drive from world-famous Clearwater Beach, offering award-winning white sand beaches, spectacular Gulf sunsets, waterfront dining, shopping, and endless recreational opportunities. This is a wonderful opportunity to enjoy comfortable Florida living in a quiet waterfront setting with easy access to everything Clearwater has to offer.

101 S Neptune Avenue, Clearwater
$449,000
3 Beds ⋅ 3 Baths ⋅ Bidwells Oak Wood Add SubDv. ⋅ 33755 Zip Code
Live in one unit and rent the other. Updated in 2017 (including roof), the property features a foyer entry dividing two separate units: a 2BR/2BA and a 1BR/1BA, each with secondary private entrances. Shared laundry room onsite. Long driveway provides ample off-street parking, plus additional street parking. Walk to downtown Clearwater events and dining, steps to the Pinellas Trail, and a short bike ride to Clearwater Beach. Excellent rental and vacation-use potential in a central, highly walkable location.

601 N Osceola Avenue, Clearwater
$487,000
4 Beds ⋅ 3 Baths ⋅ Belmont Sub 1st Add SubDv. ⋅ 33756 Zip Code
Exceptional investment opportunity with immediate upside and located just minutes from the gulf beaches! This fully leased triplex is currently generating $4,425 each month with the opportunity to increase rental income immediately. A new roof was installed in 2023 on the 1/1 building. In addition to the existing income upside, the two 1/1 units provide an excellent value-add opportunity with cosmetic updates that can further increase rents and overall property value. The property features one updated 2/1 unit (rented below market at 1,500 but could rent for 1,600) and two 1/1 units (rented at 1,425 and 1,500), offering an ideal opportunity for both seasoned investors and buyers looking to house hack/ live in one unit while the rental income from the other two helps offset their mortgage and living expenses. The updated 2/1 unit features newer windows, appliances, and flooring providing a move-in-ready option. The 2/1 unit will be vacant upon closing.Whether you're looking to expand your investment portfolio or purchase your first income-producing property, this triplex offers immediate cash flow, multiple avenues for increased returns, or the opportunity to significantly reduce your housing costs by living on-site.

725 New York St, Clearwater
$179,000
2 Beds ⋅ 2 Baths ⋅ Woodland Villas Condo 1 SubDv. ⋅ 33761 Zip Code
Active 55 and over community Villa – condo 2 bedroom with walk in closets, 2 updated bathrooms, open dining living room area. Carport right in front with additional storage area also attic has storage space. Ramp to building. There are ceiling fans in each bedroom and the Florida room. Included are a refrigerator, microwave, cooktop range, dishwasher garbage disposal. Villa has double pane windows, central air and heat, electric water heater and smoke detectors. HOA covers water, trash, cable, Internet, reserves, insurance, and exterior maintenance. Amenities are a heated pool, active clubhouse with a kitchen, social hall with many activities,and a grilling area. There is a nearby shopping area 10 minutes to countryside mall also Mease hospital with other medical facilities close by. There are many enjoyable places to go to honeymoon Island, Clearwater Beach.

2465 Northside Drive Unit 1502, Clearwater
$1,499,999
3 Beds ⋅ 2 Baths ⋅ Sunnybrook Farms SubDv. ⋅ 33764 Zip Code
Welcome to Paradise on Sunnybrook Lane!! Experience a truly one-of-a-kind Frank Lloyd Wright inspired home set on 1.5 private acres with water on two sides. Completely remodeled in 2020, this extraordinary 3bedroom, 2-bath residence was thoughtfully designed to capture natural light year-round, with expansive windows showcasing panoramic views of tranquil ponds, lush landscaping, and the resort-style backyard. As you enter the property, a beautiful fountain welcomes you at the main pond, while an elegant three-tiered fountain creates a stunning entrance to the home. Inside, distinctive angles, authentic limestone stacked stone, and dramatic architectural details reflect the timeless Prairie-style design. The centrally located kitchen overlooks the living spaces and picturesque grounds, making it the true heart of the home. The spacious primary suite features a private loft overlooking the pond, while the impressive 21’ x 26’ flex space, highlighted by soaring beams and walls of glass, offers endless possibilities as a guest suite, additional primary bedroom, studio, office, or recreation room. Step outside to your own tropical retreat featuring a spectacular 20’ x 40’ resort-style pool, two gazebos, low maintenance AstroTurf, mature coconut palms, and a private basketball/pickleball court. As evening falls, the magnificent century-old oak comes alive with thousands of twinkling lights, creating an unforgettable setting for entertaining or relaxing under the stars. This is more than a home—it’s a private waterfront sanctuary where exceptional architecture, nature, and resort-style living come together in a setting unlike any other.

1653 Sunnybrook Lane, Clearwater
$114,000
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
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