Highland Estates Homes for Sale

Highland Estates Homes for Sale

Welcome to Highland Estates, a hidden gem nestled in the heart of Florida, where the sun shines brighter and the community spirit runs deep. This enchanting subdivision is perfect for families, retirees, and everyone in between, offering a serene escape from the hustle and bustle of city life while still being conveniently close to all the amenities you could desire.

Highland Estates boasts a selection of beautifully designed homes for sale, each reflecting the charm and warmth of Floridian architecture. From spacious single-family residences to cozy townhomes, there’s something here to suit every taste and budget. Many of these homes feature open floor plans, modern kitchens, and lush backyards, ideal for entertaining or simply enjoying the gentle Florida breeze.

The neighborhood is not just about stunning homes; it’s about a vibrant community. Residents of Highland Estates enjoy access to lush parks, scenic walking trails, and recreational facilities that encourage an active lifestyle. Families will appreciate the proximity to top-rated schools, while local shops and restaurants are just a short drive away, making everyday errands a breeze.

Whether you’re seeking a peaceful retreat or a lively community atmosphere, Highland Estates has it all. Explore the homes for sale today and discover the perfect place to create lasting memories in this delightful Florida enclave. Your dream home awaits in Highland Estates—where community, comfort, and sunshine come together seamlessly!

Newest Highland Estates Homes for Sale

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

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

3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34698 Zip Code

Freshly painted throughout and featuring new flooring, this Dunedin gem is move-in ready and full of potential! This 3-bedroom, 2-bathroom home is ideally situated on a homesite backing directly to protected conservation, offering peaceful views and the rare privacy of no rear neighbors. Located within the Dunedin Golf Cart Zone, with no HOA and no deed restrictions, you’ll have the flexibility to truly make this property your own. Inside, the open-concept floor plan seamlessly connects the kitchen and living room, creating a comfortable and functional space for everyday living and entertaining. The kitchen features stainless steel appliances, plantation shutters, and modern light fixtures, while one bedroom offers brand-new vinyl flooring and a new ceiling fan. Step outside to the covered lanai and expansive concrete patio, which was extended across the full width of the home in 2022, providing plenty of space for outdoor entertaining. Approximately half of the backyard features low-maintenance ProTurf, installed just two years ago, while the fully fenced yard offers plenty of room for pets, play, and enjoying the Florida outdoors. A 6' x 16' x 8' storage shed with electricity, added in 2023, provides excellent additional storage or workspace. Additional updates include a 2020 HVAC system and updated windows and doors completed in 2014. The attached two-car garage adds everyday convenience and storage. This home is perfectly positioned near zoned schools, parks, shopping, and everyday conveniences. Downtown Dunedin is just a five-minute drive away, offering an array of restaurants, breweries, waterfront parks, and boutique shops, while Clearwater Beach is less than 20 minutes away. Whether you’re searching for a primary residence, investment property, or a home in an unbeatable location, this Dunedin property offers the perfect combination of privacy, flexibility, and convenience.

986 Lexington Drive, Dunedin

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

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

6 Beds ⋅ 3 Baths ⋅ Highland Estates SubDv. ⋅ 33598 Zip Code

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

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Shay Largie

As a Florida real estate professional with over 8 years of experience, I help clients navigate a wide range of real estate and financing needs, including first-time home purchases, new construction, investment properties, home sales, and mortgage lending. I am passionate about helping people achieve their real estate goals through expert negotiation, market analysis, financing guidance, and personalized support. My approach is rooted in servant leadership, integrity, and a commitment to providing a seamless experience from start to finish. Whether you're buying, selling, investing, or securing financing in Florida, I am dedicated to delivering exceptional service, clear communication, and trusted guidance every step of the way.

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