Highland Estates Real Estate

Highland Estates Real Estate

Welcome to Highland Estates, a picturesque subdivision nestled in the heart of Florida, where the charm of suburban living meets the allure of natural beauty. This vibrant community is designed for those who appreciate a tranquil lifestyle while still being close to the excitement of city amenities.

Highland Estates boasts beautifully landscaped streets lined with stunning homes, each reflecting a unique architectural style that contributes to the neighborhood's character. Residents enjoy spacious yards, perfect for family gatherings, gardening, or simply basking in the Florida sunshine. The community is known for its friendly atmosphere, where neighbors become friends and every street feels like home.

One of the standout features of Highland Estates is its proximity to a variety of recreational activities. With several parks and nature trails nearby, outdoor enthusiasts can indulge in hiking, biking, or leisurely strolls while soaking in the area's lush greenery. Families will appreciate the top-rated schools within a short distance, ensuring that children receive a quality education in a nurturing environment.

For those who crave a taste of urban life, Highland Estates is conveniently located near shopping centers, dining venues, and entertainment options. Whether you're in the mood for a cozy café or an evening out at a trendy restaurant, everything you need is just a stone's throw away.

Experience the perfect blend of comfort, community, and convenience in Highland Estates. Your dream home awaits in this delightful Florida subdivision, where every day feels like a vacation!

Newest Listings in Highland Estates

714 Avenue O Se, Winter Haven
$329,900
5 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 33880 Zip Code
Welcome to 714 Avenue O SE! Situated in a prime SE Winter Haven neighborhood (Polk County), this fully modernized, single-story Mid-Century Ranch features 5 bedrooms, 2 bathrooms, and 2,104 sq ft of open living space. Constructed in 1964 on a 0.32-acre lot, shaded by mature Florida oak trees, the interior includes tile flooring, central air conditioning, a wood-burning fireplace, and an updated kitchen with stainless steel appliances and solid wood cabinetry. Highlights feature an attached car garage, tankless gas water heater, impact/double-pane windows, and an indoor laundry room. Step outside to your private oasis featuring a fully renovated in-ground pool, screened lanai, open patio, and brand-new privacy-fenced backyard. Conveniently zoned for Chain of Lakes Elementary and Winter Haven Senior High!

714 Avenue O Se, Winter Haven
14441 Alistar Manor Drive, Wimauma
$250,000
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 33598 Zip Code
SELLER IS OFFERING UP TO $10,000 IN SELLER CONCESSIONS! Welcome to 14441 Alistar Manor Dr, a charming 3-bedroom, 2-bathroom home located in the desirable Ayersworth community of Wimauma! This inviting home features a comfortable and functional layout with plenty of space to make your own. Step outside to a large backyard offering plenty of room for entertaining, outdoor activities, gardening, or simply enjoying the Florida sunshine. Ayersworth offers an impressive selection of community amenities, including a resort-style swimming pool, fitness center, basketball courts, tennis court, and playground. Conveniently located near restaurants, shopping, and everyday essentials, the community also offers easy access to I-75 for travel north toward Tampa or south toward Bradenton and Sarasota. Whether you're purchasing your first home, looking for more space, or simply want to enjoy a community filled with amenities, 14441 Alistar Manor Dr is ready to welcome you home. Schedule your private showing today!

14441 Alistar Manor Drive, Wimauma
9637 Passaic Drive, Hudson
$228,985
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34667 Zip Code
Country living! This turnkey, fully remodeled 3-bedroom, 2-bathroom home sits on an impressive peaceful .45-acre lot. BRAND-NEW BIG-TICKET ITEMS include a NEW ROOF, NEW WATER TREATMENT SYSTEM, and NEW HOT WATER HEATER. Interior highlights include BRAND NEW bathrooms with spa-inspired showers, NEW luxury vinyl plank flooring throughout, granite countertops, stainless steel appliances, new contemporary fixtures, fresh interior paint, and an open floor plan with abundant natural light. The property also features a private well and septic system, reducing monthly utility costs, plus a large lockable storage shed. With no HOA and low property taxes, this home offers added flexibility and huge affordability benefits. The owner is completing the legal conversion from personal property to real property, commonly known as “detitling” or retiring the mobile-home title. Once completed/recorded, the home will be permanently affixed to the land and treated as real property. This allows more financing options/potential financing through FHA, VA, conventional, or other loan programs, subject to lender approval. Agricultural zoning provides room for a homestead-inspired lifestyle, including chickens and other permitted livestock, as well as parking for an RV, boat, or work vehicle. The spacious lot may also offer future potential for a detached garage, workshop, or ADU. Enjoy privacy and room to grow while remaining conveniently located near well rated schools, shopping, dining, medical facilities, major highways, and Gulf Coast beaches. Whether you’re seeking a full-time residence, winter retreat, or property with space for future plans, this home offers comfort, flexibility, and opportunity.

9637 Passaic Drive, Hudson
986 Lexington Drive, Dunedin
$435,000
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
961 Lexington Drive, Dunedin
$425,000
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv. ⋅ 34698 Zip Code
Back on the market! No fault of the sellers. Buyer's financing fell through. All 4-point repairs have been made! Clean house! Bring all 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
10657 Standing Stone Dr, Wimauma
$399,999
6 Beds ⋅ 3 Baths ⋅ Highland Estates SubDv. ⋅ 33598 Zip Code
Motivated Sellers!! Come look at 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 in the Tampa Bay area . *Paid Solar Panels *

10657 Standing Stone Dr, Wimauma
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