Highland Estates Homes for Sale

Highland Estates Homes for Sale

Welcome to Highland Estates, a hidden gem nestled in the heart of Florida, where charm meets modern living! This picturesque subdivision is renowned for its lush landscapes, friendly community atmosphere, and a variety of amenities that cater to every lifestyle. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Highland Estates has something for everyone.

The homes for sale in Highland Estates boast a diverse range of architectural styles, from contemporary designs to classic Florida ranch homes. Each property features spacious layouts, inviting outdoor spaces, and modern finishes that create a perfect blend of comfort and elegance. Imagine sipping your morning coffee on a sun-drenched patio or hosting weekend barbecues in your expansive backyard – the possibilities are endless!

Residents of Highland Estates enjoy access to a wealth of community amenities, including beautifully maintained parks, walking trails, and recreational facilities. The subdivision is conveniently located near top-rated schools, shopping centers, and dining options, making it an ideal place to call home. Plus, with Florida's stunning beaches and vibrant cultural attractions just a short drive away, you’ll never run out of things to explore.

Don’t miss your chance to join this thriving community! With homes for sale in Highland Estates, you can find the perfect place to create lasting memories. Explore your options today and discover why so many are choosing to call Highland Estates home. Your dream home awaits in this enchanting Florida paradise!

Newest Highland Estates Homes for Sale

$545,000
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34698 Zip Code
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
$459,000
4 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34698 Zip Code
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
$444,000
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34698 Zip Code
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
$1,050,000
5 Beds ⋅ 5 Baths ⋅ Highland Estates SubDv. ⋅ 32779 Zip Code
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
Start Your Search