Highland Estates Real Estate

Highland Estates Real Estate

Welcome to Highland Estates, an enchanting subdivision nestled in the heart of Florida, where the sun shines bright and community spirit thrives. This picturesque neighborhood is characterized by its lush landscapes, pristine tree-lined streets, and a warm, inviting atmosphere that makes it a perfect place to call home.

Highland Estates offers a diverse selection of beautifully designed homes, from charming single-family residences to more spacious estates, catering to a variety of lifestyles and preferences. Each property boasts modern amenities and unique architectural styles, ensuring that every homeowner finds their perfect sanctuary. The thoughtfully planned layout of the community encourages a sense of belonging, with friendly neighbors and a welcoming vibe that makes it easy to create lasting connections.

The location of Highland Estates is truly unbeatable. Residents enjoy easy access to a wealth of nearby attractions, including stunning beaches, vibrant shopping districts, and delectable dining options. Outdoor enthusiasts will appreciate the proximity to lush parks and nature trails, perfect for leisurely strolls, picnics, or family outings.

Families with children will find that Highland Estates is located within highly-rated school districts, providing excellent educational opportunities for all ages. The community also hosts various events and activities throughout the year, fostering a strong sense of camaraderie among residents.

Whether you’re looking for a peaceful retreat or an active lifestyle, Highland Estates is the ideal place to settle down in Florida. Discover the charm of this community and make it your own – your dream home awaits!

Newest Listings in Highland Estates

$545,000
3 Beds ⋅ 2 Baths ⋅ TB8532566 MLS
Welcome to 57 Ventura Dr, where thoughtful updates, inviting outdoor living, and the laid-back Dunedin lifestyle come together. This well-maintained home features several valuable improvements, including a **new roof, newer air-conditioning system and new pool pump**, offering added comfort and peace of mind for years to come. Step outside and enjoy your own private backyard retreat. The swimming pool provides the perfect setting for cooling off on warm Florida afternoons, entertaining friends and family, or simply relaxing at home. New landscaping adds fresh curb appeal and creates an attractive first impression. Ideally located near charming Downtown Dunedin, residents can enjoy local restaurants, breweries, boutiques, waterfront parks, the Pinellas Trail, and nearby Gulf beaches. Whether you are searching for a primary residence, seasonal getaway, or investment opportunity, this updated Dunedin home delivers the location, lifestyle, and major improvements today’s buyers are looking for. Schedule your private showing and discover everything 57 Ventura Dr has available to you.

57 Ventura Drive, Dunedin
$475,000
4 Beds ⋅ 2 Baths ⋅ TB8531611 MLS
Virtually Staged. Welcome to this beautifully renovated 4-bedroom, 2-bathroom home in desirable Dunedin! This move-in-ready property has been thoughtfully updated with new roof (2025), new windows (2025), fresh exterior paint (2026), and a completely updated interior featuring new flooring, modern finishes throughout, updated kitchen and bathrooms, and convenient interior laundry. The spacious fenced backyard is easily accessible through the new French doors leading from the living room, creating the perfect indoor-outdoor Florida living space. Located within the Dunedin golf cart zone and just minutes from downtown Dunedin, TD Ballpark, shopping, dining, and the Gulf beaches, this home offers the perfect combination of timeless updates, comfort, and an unbeatable location. Owner/agent. One or more photos was virtually staged.

19 Ventura Drive, Dunedin
$749,900
3 Beds ⋅ 4 Baths ⋅ A12054001 MLS ⋅ Old Florida Village BLDG.
Nestled in the sought-after boutique community of Old Florida Village, this 3-bedroom, 3.5-bath townhome sits in the heart of Wilton Manors. Bright and welcoming, it boasts 9-foot ceilings, crown molding, recessed lighting, a two-car garage, and dual-zone AC. The open-concept main living area features a kitchen with granite countertops and stainless-steel appliances. Impact windows throughout. A second master bedroom with a full bath on the first floor is perfect for guests or family. The top-floor master suite offers two walk-in closets and a luxurious bath with dual sinks and a separate tub and shower. Engineered wood, tile, and carpet flooring. 2 Car driveway with 2 Car garage. The AC and water heater are approximately six years old. Interior sprinkler system for safety. With only 18 homes in the community, it’s within walking distance to the excitement of Wilton Drive and just a short drive to the beach—a fantastic place to call home!

2726 Old Florida Trail, Wilton Manors
$575,000
3 Beds ⋅ 4 Baths ⋅ B26051261 MLS ⋅ Palm Island Villas BLDG.
Three-story townhouse centrally located in Wilton Manors just off Wilton Drive! Enjoy 2,294 square feet of living space with 3 BR and 3.5 BA, offering plenty of room for everyday living & entertaining. On the first level you'll find a spacious two-car garage and a bedroom with an en-suite bathroom, making it ideal for guests or home office/flex space. The second floor offers a light-filled open floor plan w/ two balconies, kitchen, dining area, living room, & half bath. The third level features a secondary bedroom with its own en-suite bathroom, along w/ an expansive primary suite offering tray ceilings, a large ensuite bath, and a generous walk-in closet. Freshly painted throughout with brand-new carpeting in the bedrooms. Central courtyard w/ heated pool.

2725 NE 8th Avenue Unit 104, Wilton Manors
$849,900
4 Beds ⋅ 4 Baths ⋅ B26043330 MLS ⋅ Pelican Perch BLDG.
Spacious, and rarely available Pelican Perch, multi-level townhome just steps to Wilton Drive. Almost 3,000 sf of living space1 Features two generous sized primary suites, huge amounts of closet space, an additional bedroom and full bath on the top level, lower level office/bedroom, two car garage, and a massive roof top terrace with amazing views. Large eat-in kitchen overlooking the expansive living area, bar seating and newer appliances. Wood flooring, granite and tile finishes, high ceilings, outside garden area, balconies, two newer air conditioning units, freshly painted and move in ready. Low HOA fee and only 9 units in the complex.

2700 NE 8th Avenue, Wilton Manors
$444,000
3 Beds ⋅ 2 Baths ⋅ TB8512558 MLS
MOTIVATED SELLERS! BRING YOUR OFFERS! Must see to truly appreciate! Step into this 3-bed, 2-bathroom slice of paradise nestled underneath grand oak trees in delightful Dunedin. This home has old Florida charm without sacrificing modern amenities. Located in the coveted GOLF CART ZONE in one of the most sought-after areas in the Tampa Bay region. Conveniently situated with a short golf cart ride or walk to everything that Dunedin has to offer but far enough away to have the peace and quiet when wanted. Open floor plan with tons of natural light. The cozy kitchen boasts granite countertops with stainless steel appliances, under-cabinet recessed lighting and a tavern-height breakfast bar. Through one of the two living areas, you’ll pass through double French doors to your roughly 19x35 enormous patio with a metal gazebo already included. That’s over 650 square feet of endless options. Plenty of space to put in an outdoor kitchen, hot tub, or both. You will also be able to cool off in the sparkling pool! The backyard is completely fenced in with 6ft vinyl privacy fence that keeps you totally secluded from neighbors and passersby. This home has been meticulously maintained and is turnkey ready! Major updates include a new roof and PGT hurricane-impact-resistant windows and doors in 2019. A new Carrier Infinity HVAC system in 2021, and a new Rheem hot water heater in 2023. The garbage disposal and dishwasher were also replaced in 2026. This gem also sits high and dry in an X non-evacuation flood zone. Located just .08 miles to TD Ballpark, where the Toronto Blue Jays play spring training games, 1 mile to downtown, where you can enjoy breweries, multiple restaurants and bars, shopping, and the beautiful Dunedin Marina. Along with multiple parks and the Pinellas Trail, you’ll never run out of things to do. Just a 15-minute drive to both Clearwater Beach and Honeymoon Island and everything else that Pinellas County has to offer. Don’t miss out on this one!

961 Lexington Drive, Dunedin
$89,000
3 Beds ⋅ 2 Baths ⋅ A4692365 MLS
Exceptional opportunity to own nearly an acre (.90 acres) of land with no HOA, no lot rent, and located outside of a flood zone. The true value is in the land and existing impact fees, offering incredible potential for future development—including the possibility to split this spacious double lot (buyer to verify). With an expansive driveway and generous lot size, this property is ideal for building your custom dream home while still enjoying privacy and flexibility. Conveniently located near US-19 and Little Road, providing easy access to New Port Richey, Tarpon Springs, Dunedin, and Clearwater—making commuting, shopping, dining, and beaches all within reach. Septic and well inspection reports are available upon request.

9918 Fargo Drive, Hudson
$1,050,000
5 Beds ⋅ 5 Baths ⋅ O6390329 MLS
Welcome to 814 Miami Springs Drive, an exceptional private estate nestled in one of Longwood’s most desirable locations near the Wekiva River and Wekiva Island. Positioned on a beautifully landscaped homesite backing to a tranquil natural preserve, this residence offers a rare blend of elegance, privacy, and resort-style living with no HOA restrictions. This impressive five-bedroom, five-bathroom residence with a loft was thoughtfully designed with both comfort and sophistication in mind. From the moment you enter, the home showcases soaring ceilings, expansive living spaces, and refined architectural details that create an inviting yet grand atmosphere. The main living areas flow effortlessly, providing an ideal setting for both everyday living and entertaining. The spacious chef’s kitchen features a large center island, generous cabinetry, and seamless connection to the surrounding living and dining areas, allowing gatherings to feel both open and intimate. The primary suite serves as a private retreat, offering a luxurious bathroom complete with dual vanities, a soaking tub, walk-in shower, and generous closet space designed for comfort and functionality. Upstairs, a versatile loft space provides endless possibilities and could function beautifully as a media room, executive home office, or additional lounge area. Outside, the home transforms into a private outdoor sanctuary. A screen-enclosed resort-style pool and spa are framed by an expansive covered lanai, creating a perfect setting for relaxation and entertaining while overlooking the lush preserve beyond. With no rear neighbors, the backyard delivers a level of privacy that is increasingly rare while still being moments from everyday conveniences. The home offers five spacious bedrooms, five bathrooms, and a flexible loft layout, all complemented by grand ceiling heights, elegant architectural detailing, and thoughtfully designed living areas. The preserve backdrop enhances the sense of tranquility, while the screened pool and outdoor living space allow you to fully embrace the Florida lifestyle. Located just minutes from Wekiva Island, Wekiva Springs State Park, scenic trails, dining, and shopping, this property offers a lifestyle centered around nature, privacy, and refined living. A rare opportunity to own a luxury estate near the Wekiva River where space, tranquility, and convenience come together seamlessly.

814 Miami Springs Drive, Longwood
$420,000
6 Beds ⋅ 3 Baths ⋅ TB8465219 MLS
Massive Price Drop!! Welcome to this freshly painted, well-maintained 6-bedroom, 3-bath single-family home located in the peaceful community of Wimauma, where space, comfort, and convenience come together. With a generous layout, this home is ideal for large families, multi-generational living, or anyone needing extra rooms for a home office, gym, or guest space. The kitchen features granite countertops and a full appliance package, offering a functional and stylish hub for everyday living and entertaining. Spacious living areas flow seamlessly throughout the home, while six versatile bedrooms provide flexibility to suit your lifestyle. Three full bathrooms add comfort and ease for busy households. Step outside and enjoy a location surrounded by natural beauty and outdoor recreation, including nearby Little Manatee River State Park, scenic walking trails, and easy access to kayaking, hiking, and wildlife viewing. Just a short drive away, you’ll find Apollo Beach, Ruskin waterfront dining, and Gulf Coast beaches, along with shopping and dining options in Riverview and Brandon. Downtown Tampa, sporting events, and cultural attractions are also within easy reach. Move-in ready, freshly updated, and ideally located, this home offers the perfect blend of quiet Florida living with access to everything the Tampa Bay area has to offer. * Solar Panels to be paid off at closing**

10657 Standing Stone Dr, Wimauma
$155,000
2 Beds ⋅ 2 Baths ⋅ W7876582 MLS
Cash buyers, take a look at this one!! MOVE IN READY!! High and dry, no flood insurance required, yet under 5 miles to Hudson Beach and Marina or Sun West for kayaking, ski jumping and more!! No HOA! No lot rent! New roof (2024). Motivated seller!! Quiet corner lot, fully chain-linked and privacy-fenced with a huge double gate to pull in and park your toys! This home has beautiful tile floors and lifetime waterproof flooring throughout!! A gorgeous three-season lanai with the windows tinted or open them to enjoy the breeze. This home has been very well-maintained. The yard is ample for your animals to roam, for you to entertain, or for whatever your future visions happen to be!! Plenty of storage with three large sheds on the property! Schedule your private showing today!

9507 Passaic Drive, Hudson
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