Highland Estates Homes under $500,000

Highland Estates Homes under $500,000

Welcome to Highland Estates, a hidden gem nestled in the heart of Florida, where charm meets affordability! This vibrant subdivision offers a perfect blend of serene living and modern conveniences, making it an ideal choice for families, retirees, and everyone in between.

Highland Estates is characterized by its picturesque streets lined with lush greenery and well-maintained homes, creating a welcoming atmosphere that’s hard to resist. Here, you’ll find a variety of beautifully designed residences, many of which are priced under $500,000. This makes it an exceptional opportunity for first-time homebuyers or those looking to downsize without compromising on quality or comfort.

The homes in Highland Estates boast spacious layouts, contemporary finishes, and inviting outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars. With a diverse selection of styles, from cozy single-family homes to charming townhouses, there’s something to suit every taste and lifestyle.

Beyond the beautiful homes, Highland Estates is conveniently located near shopping centers, dining options, and recreational facilities, ensuring that everything you need is just a stone's throw away. Families will appreciate the proximity to top-rated schools and parks, fostering a strong sense of community and providing endless opportunities for outdoor activities.

Whether you’re looking to plant your roots or find a peaceful retreat, Highland Estates offers an exceptional living experience without breaking the bank. Discover the joys of affordable Florida living today—your dream home awaits in Highland Estates!

Newest Highland Estates Homes under $500,000

714 Avenue O Se, Winter Haven
$329,900
5 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv.
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
27968 Lance Drive, Bonita Springs
$468,000
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv.
Nestled in the heart of Bonita Springs just off Bonita Beach Rd, this wonderful home presents comfortable living with convenient access to all the best the area has to offer—pristine beaches, vibrant shopping, and easy connections to 41, I-75 and Fort Myers Airport are all within reach. Step outside into your private sanctuary where the LARGE BACK YARD truly comes alive: a beautifully landscaped tropical paradise bathes in warm west-facing sunlight, complete with enchanting landscape lighting that brings the outdoor spaces to life after dark and a spacious screened lanai that extends your living space year-round. There is also room for a pool and spa. The interior gleams with thoughtfully upgraded cabinetry, tile flooring and stainless-steel appliances including a brand-new refrigerator. The garage has an impressive epoxy garage floor featuring convenient pull-down steps to the attic for easy storage access. This gem comes with the added peace of mind of *NO HOA fees, NO CDD fees and NO Flood insurance required* giving you the freedom and financial flexibility to truly make this your own. With its blend of modern comfort, tropical charm, and practical amenities, this Bonita Springs home invites you to embrace the Florida lifestyle you've always dreamed of.

27968 Lance Drive, Bonita Springs
14441 Alistar Manor Drive, Wimauma
$250,000
3 Beds ⋅ 2 Baths ⋅ Highland Estates SubDv.
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.
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.
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.
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.
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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