Highland Lakes Homes under $500,000

Welcome to Highland Lakes, a picturesque subdivision nestled in the heart of sunny Florida, where tranquil living meets vibrant community life. This hidden gem offers a perfect blend of natural beauty and modern convenience, making it an ideal destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

Highland Lakes is characterized by its lush landscapes, serene lakes, and friendly neighborhoods. Residents enjoy a wealth of recreational opportunities, including walking trails, parks, and community amenities that foster a sense of belonging. The community is known for its welcoming atmosphere, where neighbors become friends and every day feels like a vacation.

One of the most appealing aspects of Highland Lakes is the range of homes available for under $500,000. This affordability allows you to find your dream home without breaking the bank. Whether you're seeking a cozy single-family residence, a spacious townhome, or a charming villa, Highland Lakes has something for everyone. Many of these homes feature modern designs, open floor plans, and beautiful outdoor spaces, perfect for entertaining or relaxing in the warm Florida sun.

Living in Highland Lakes means you're just a short drive away from the beautiful Gulf Coast beaches, shopping centers, and a variety of dining options. With excellent schools and a strong sense of community, this subdivision is not just a place to live—it's a place to thrive. Discover the enchanting lifestyle that awaits you in Highland Lakes, where your dream home is within reach!

Newest Highland Lakes Homes under $500,000

$252,000

3 Beds ⋅ 2 Baths ⋅ G5118903 MLS

Welcome to this spacious and inviting home which will impress you from the moment you walk in through the porcelain tiled entryway. Gorgeous wood flooring and neutral colors and the 2 skylights add a bright, welcoming atmosphere and the stage for comfortable living. The kitchen, with its porcelain tile, opens seamlessly to the dining area and highlights the updated appliances including a gas stove, a double oven and its own breakfast nook. Major updates provide peace of mind, including a 2022 roof, a 2026 HVAC system, an updated Siemens electrical box and a 2013 water heater. The 2-car garage offers a remote electric garage door screen. The home also has a whole-house water softener. The enclosed lanai with custom privacy shades is a perfect spot to relax while barbequing on the patio or enjoy the water view from the front porch as you wave and get to know your neighbors as they enjoy their walks. Both bedrooms are ample sized with carpeting and are comfortable, and relaxing. The front bedroom offers a beautiful water view. The roomy guest bathroom hosts a shower, tub and a bidet. The large primary suite offers comfort with plenty of storage and an ensuite bathroom with a walk-in shower and its own make-up area. Highland Lakes is one of Lake County’s most established and rich amenity 55+ communities offering an impressive array of amenities for only $135- a month. Residents enjoy the sparkling indoor and outdoor pools along with a spacious clubhouse with a fitness center, game and meeting rooms, billiards and ping pong, a craft room with a kiln, an extensive library, a catering kitchen, an indoor arena with a stage for live entertainment and community events. Outdoor amenities include walking trails, fishing ponds, lighted tennis and pickleball courts, shuffleboard, bocce ball, horseshoe pits, a softball field with concession stand, a covered picnic pavilion with grills, a Craftsmen Club / Wood Working Shop (join for just $12 annually), an RV and boat storage (included in HOA), a golf driving range and catch and release fishing lakes. Enjoy the peaceful surroundings of Highland Lakes which are designed for an engaging lifestyle. Schedule a showing today!

26162 Newcombe Circle, Leesburg

Listing courtesy of FLORIDA PLUS REALTY, LLC. 407-252-2596

$299,990

3 Beds ⋅ 2 Baths ⋅ TB8556354 MLS

Virtually Staged. Completely renovated and packed with upgrades, this 3-bedroom, 2-bathroom Weeki Wachee home delivers the perfect blend of modern style and outdoor living! Featuring a brand-new roof and HVAC, an open layout, soaring vaulted ceilings, a split-bedroom floorplan, and a 2-car garage, this home is ready for its next owner. The beautifully updated interior features fresh paint inside and out, new flooring, lighting, and ceiling fans throughout. The showstopping kitchen boasts sleek new cabinetry, gorgeous quartz countertops, stainless steel appliances, a breakfast bar, and a spacious island with additional seating and storage. Both bathrooms have also been tastefully remodeled with tiled showers, stylish new vanities, and modern finishes. Step outside to the large covered and screened wooden deck, where you can unwind, entertain, or fire up the grill while enjoying peaceful lake views. Need extra room for your toys? The detached carport is perfect for storing an additional vehicle, boat, or other recreational gear. Love the outdoors? You're in the right place! Enjoy kayaking, swimming, and the famous mermaid shows at Weeki Wachee Springs State Park, spend a day at Pine Island Park, or head to nearby Gulf beaches and public boat ramps just 10–15 minutes away. Fishing, boating, and spectacular sunsets are all within easy reach! Shopping, dining, medical facilities, and major roadways are close by, with Spring Hill just a short drive away. Fresh renovations, a lake-view backyard, and peaceful Florida living await!

8221 Normandy Drive, Brooksville

Listing courtesy of LOKATION. 954-545-5583

$414,900

3 Beds ⋅ 2 Baths ⋅ TB8555772 MLS

Amazing 3/2/2 Home in 55+ desirable community with no flood and many activities, including 3 nine hole executive golf courses for only $164 per month. The home has had many updates including both baths and kitchen remodeled in 2024.Mostly newer windows 2026 and many other updates. Enter the home at the foyer and see luxury vinyl floors, track lighting and lots of closet space. The Master Bedroom has a Walk-in Closet with shelves and Walk-in Shower. Relax and enjoy the private Screened Lanai Flat Roof 2024, A/C approx 3 years, sprinklers on reclaimed water. Freshly painted and ready to move in. Amenities include Community Pool, Hot Tub and Activities such as bingo, cornhole, concerts, dances, breakfast events & over 40 activities! Walk, bike or drive to the lodge on Lake Tarpon where they have a Clubhouse, Pontoon boats, boat & RV storage, dock, grills & more!

1529 E Dorchester Drive, Palm Harbor

Listing courtesy of BAY TO SHORE PROPERTY MANAGEMENT AND LEASING LLC. 727-422-7120

$365,000

2 Beds ⋅ 2 Baths ⋅ TB8554386 MLS

Virtually Staged. Welcome to 913 Sutton Place! Impeccably clean, beautifully updated, and truly move-in ready, this 2-bedroom, 2-bathroom villa in the highly desirable 55+ community of Highland Lakes offers comfortable Florida living with access to an incredible array of amenities. The beautifully remodeled kitchen features quartz countertops, white shaker cabinetry, and tile flooring, creating a bright and inviting space that opens effortlessly to the main living areas. Plantation shutters and engineered hardwood flooring add warmth and character throughout the living room, while tile flooring in the bedrooms provides easy maintenance and durability. Additional improvements include a newer front entry door, two newer front windows, updated screening on both the front porch and screened-in back lanai, and beautiful landscaping with multiple palm trees. Major updates include a 2020 roof and 2016 A/C, providing added peace of mind. The home also features a one car garage and has a golf cart pad! Highland Lakes is one of Palm Harbor’s most sought-after 55+ communities, offering resort-style amenities including three professionally maintained private executive golf courses, heated pools and spa, shuffleboard, bocce ball, RV and boat storage, a vibrant clubhouse, and an extensive lineup of clubs and activities. Residents also enjoy exclusive access to Lake Tarpon with a private boat ramp and fishing pier, an incredible amenity that truly sets this community apart. Beautifully maintained, thoughtfully updated, and ready for its next owner, 913 Sutton Place is the perfect place to enjoy the Florida lifestyle. Schedule your private showing today!

913 Sutton Place, Palm Harbor

Listing courtesy of KATIE DUCHARME REALTY, LLC. 727-744-2214

$314,900

3 Beds ⋅ 2 Baths ⋅ 2167426 MLS

Spacious 3 BR 2BA home with functional, split floor plan in Argyle/Oakleaf area. Tucked away in a cul-de-sac in Highland Lakes. Enjoy your own backyard get away with a gathering area surrounding a fire pit, an expansive deck bordering an above ground pool and a huge fully fenced backyard! Newer roof, New HVAC!

8189 Kilwinning Lane, Jacksonville

Courtesy of UNITED REAL ESTATE GALLERY

Listing courtesy of UNITED REAL ESTATE GALLERY.

Listing courtesy of DANIELLE L TORRES from UNITED REAL ESTATE GALLERY.

$249,999

3 Beds ⋅ 2 Baths ⋅ TB8553918 MLS

Welcome home to this charming beautifully renovated 3 BEDROOM, 2 BATH manufactured home sits on a generous 0.7-acre FENCED CORNER LOT offering the perfect blend of comfort, functionality, and Florida charm with a beautiful CIRCULAR DRIVEWAY. NO HOA, No CDD, No Flood Zone. Step inside to find a thoughtfully updated interior featuring a stunning UPDATED KITCHEN ISLAND deal for entertaining or casual family meals and holiday gatherings with an Open Concept and Vaulted ceiling. Outside, the expansive corner lot provides plenty of room to enjoy Florida's beautiful year-round weather, whether you're relaxing in your own backyard oasis or hosting friends and family. Includes a 10'x16' Loft/Barn style shed for workshop/storage. for extra space for tools, toys, or hobby gear, keeping your home organized. There's plenty of space for your RV/Boat or both! Less than an hour to Tampa! The home is fenced and is move-in ready, be sure to bring your pet(s). LOCATION is everything, and this property delivers, you're just minutes from schools, shopping, and everyday conveniences, and only 2 miles from the world-famous Weeki Wachee Springs State Park, home of the legendary mermaid shows. Roof (2022) AC (2026) updated Septic system. Homes like this combining a prime location, a huge lot, and move-in-ready updates don't last long. Schedule your private showing today!

9918 Osceola Drive, Brooksville

Listing courtesy of RE/MAX MARKETING SPECIALISTS. 352-686-0540

$400,000

2 Beds ⋅ 2 Baths ⋅ TB8551583 MLS

Welcome to Highland Lakes, a 55+ community on Lake Tarpon, where comfortable Florida living meets an incredible active-adult lifestyle. This 2-bedroom, 2-bath home offers 1,376 square feet of living space, plus a BONUS ENCLOSED FLORIDA ROOM (not included in square footage). Enjoy your morning coffee, entertain guests, pursue a hobby or simply relax while taking in the surrounding Florida nature and wildlife. The home is located in FLOOD ZONE X and features IMPACT WINDOWS, NEW WATERPROOF VINYL FLOORING, A 3-YEAR-OLD ROOF and a GENERATOR SUBPANEL for added peace of mind. Highland Lakes offers an exceptional array of amenities all included in the low HOA fee. Enjoy unlimited resident golf on three private executive courses or try your hand at tennis, pickleball, bocce and shuffleboard. Take a dip in the olympic-size geothermal-heated pool or spa and mingle with new friends. The clubhouse offers billiards, arts and crafts, woodworking, a lending library and access to the community's lakeside Lodge. Take a tour of Lake Tarpon on the community pontoon boat, and enjoy RV AND BOAT PARKING available to residents, making it easy to enjoy the best of the Florida lifestyle both on and off the water. And then there's the LOCATION, LOCATION, LOCATION. You're approximately 15 minutes from award-winning Gulf Coast beaches, perfect for sunset watching. Head north to the famous Sponge Docks of Tarpon Springs for restaurants and shopping, or south to charming Dunedin for boutique shops, restaurants and entertainment. Innisbrook Golf & Spa Resort is just minutes away, so grab your tickets for the Valspar Championship. Pinellas County parks, Lake Tarpon, cultural attractions, museums, galleries and Tampa Bay's many dining and entertainment destinations are all within easy reach. Tampa International and St. Pete-Clearwater airport are just a short drive away. With the important upgrades already taken care of, all that's left is to pack your bags, clear your calendar and start enjoying the golf, beaches, boating and everything else this incredible Florida lifestyle has to offer.

1382 Glengarry Drive, Palm Harbor

Listing courtesy of TAM BAY REALTY LLC. 813-493-2913

$459,900

2 Beds ⋅ 2 Baths ⋅ TB8549269 MLS

Attention Investors currently rented! Discover the perfect blend of comfort, style, and community in this beautifully renovated home, nestled in Palm Harbor’s premier 55+ golf community. From the moment you step inside, you’ll notice the thoughtful upgrades: fresh paint, new interior doors, elegant crown molding, and brand-new bathrooms. Luxury vinyl floors flow throughout, while abundant natural light and a rare wood-burning fireplace add warmth and charm. The updated kitchen is a true highlight, featuring granite countertops, self-closing cabinets, and new stainless steel appliances. It opens seamlessly to a cozy sitting area and the oversized Florida Room—perfect for hosting friends or simply enjoying a quiet morning coffee. Your spacious master suite is a private retreat with a den/office, walk-in closet, and spa-style bath with a step-in shower. Say goodbye to popcorn ceilings—this home has been fully modernized with today’s finishes. Major systems have been taken care of so you can move in with confidence: a newer electrical panel, on-demand water heater (2025), HVAC (2020), and a whole-house water filtration system. The roof is protected with Roof Max coating, extending its life and providing peace of mind. Add in a cost-saving deep-water well, and this home is truly turn-key. Highland Lakes is known as Tampa Bay’s best value in 55+ living. Residents enjoy free green fees on three private executive golf courses, plus pickleball, tennis, bocce, shuffleboard, 3 pools and beginner clinics to try something new. The clubhouse buzzes with fitness classes, entertainment, and social events, while the Arts & Crafts Annex features woodworking and creative studios. At Lake Tarpon Lodge, you’ll find a heated pool, fishing pier, picnic areas, and community pontoon boats. Free RV and boat storage, a secure lot, and a private boat ramp make life here even more convenient. This isn’t just a house—it’s a gateway to the lifestyle you’ve earned.

2866 Thistle Court N, Palm Harbor

Listing courtesy of KNOWN REAL ESTATE LLC. 813-787-4451

$264,900

2 Beds ⋅ 2 Baths ⋅ 2164538 MLS

Charming Waterfront Opportunity! This beautifully updated 2-bedroom, 2-full-bath home offers comfort, style, and low-maintenance living in a convenient Jacksonville location. Freshly painted inside with modern colors, the home features a completely renovated primary shower with contemporary finishes, new stainless-steel appliances, and luxury LVP flooring throughout--no carpet to replace! The spacious living room boasts vaulted ceilings and a cozy fireplace, creating a warm and inviting atmosphere. Enjoy added peace of mind with a 2023 roof and 2019 HVAC system. Step outside to the spacious, beautifully crafted concrete screened patio, perfect for entertaining, relaxing, or enjoying peaceful waterfront evenings. Conveniently located near Oakleaf Town Center with shopping, dining, entertainment, and everyday conveniences nearby. Don't miss this wonderful waterfront opportunity!

8047 Mactavish Way E, Jacksonville

Courtesy of SUPREME PATH BROKERAGE LLC

Listing courtesy of SUPREME PATH BROKERAGE LLC.

Listing courtesy of CHETAN PATEL from SUPREME PATH BROKERAGE LLC.

$425,000

2 Beds ⋅ 2 Baths ⋅ TB8547051 MLS

Welcome to this spacious and well-maintained 2-bedroom, 2-bath home in the highly sought-after 55+ community of Highland Lakes! This home offers over 1,700 heated square feet of living space, a flexible office that could also serve as a third bedroom, and plenty of room to make it your own. Nestled on a quiet cul-de-sac with no through traffic, the property features an oversized, nearly quarter-acre lot. Inside, you'll find a versatile floor plan with both a formal living room and a comfortable family room, along with a large Florida room overlooking the spacious backyard. The generously sized primary suite offers plenty of room for a king-size bedroom set, a walk-in closet, an additional built-in closet, and a private en-suite bath with a walk-in shower. The split-bedroom layout provides privacy for guests, with the second bedroom located on the opposite side of the home and conveniently positioned near the hall bath with a tub/shower combination. A 2021 ROOF and location in a non-flood and non-evacuation zone provide added peace of mind. And then there's the Highland Lakes lifestyle! With an incredibly affordable HOA fee of only $164 per month, residents enjoy unlimited FREE golf on three private executive courses, plus tennis, pickleball, bocce, shuffleboard, fitness classes, entertainment, clubs, and countless social activities at the vibrant clubhouse. The private Lake Tarpon Lodge offers a boat ramp, fishing pier, and community pontoon boats, while complimentary RV and boat storage and golf cart-friendly streets make enjoying the community even easier. Ideally located just minutes from beautiful Gulf beaches, shopping, dining, healthcare, professional sporting venues, two international airports, and a cruise port, this home offers an incredible opportunity to enjoy the best of the Florida lifestyle. This home is ready for your personal touch - come see all this wonderful home and exceptional community have to offer!

1745 Dugall Court, Palm Harbor

Listing courtesy of COLDWELL BANKER REALTY. 727-781-3700

$395,000

2 Beds ⋅ 2 Baths ⋅ TB8543762 MLS

Virtually Staged. A MUST SEE! Beautifully updated and move-in ready with a charming cottage feel, this 2-bedroom, 2-bath home is nestled in Palm Harbor’s premier 55+ golf community of Highland Lakes. Freshly landscaped and thoughtfully updated, the home welcomes you through an elegant glass front door into a bright, open-concept living space filled with natural light. Fresh modern interior paint, chair rail accents, new fans and fixtures, updated door hardware, and smooth ceilings (no popcorn!) add to the home’s timeless appeal! The spacious Florida room offers peaceful, private green views through hurricane-impact windows and opens through double glass doors to a fully enclosed lanai, not included in the living square footage, providing additional space for relaxing or entertaining. The oversized 1-car garage is truly exceptional, featuring BRAND-NEW epoxy flooring, freshly painted walls, a BRAND-NEW exterior garage door, and a BRAND-NEW mini-split AC system that keeps the space ice cold year-round—perfect for a workshop, hobby space, or additional storage! The beautifully updated kitchen features quartz countertops, solid wood cabinetry, a large pantry, tray ceiling, and a bright eat-in dining nook. The generous primary suite offers a BRAND-NEW renovated walk-in shower, BRAND-NEW vanity with stone countertop, spacious walk-in closet, and an additional built-in closet for plenty of storage. MAJOR updates include a 2019 HVAC system, 2018 electrical panel, hurricane-impact windows, and a cost-saving deep well. Situated in a non-evacuation, high-and-dry zone, this home offers added peace of mind. Highland Lakes offers an exceptional active 55+ lifestyle with a remarkably low HOA fee of just $164/month, including unlimited FREE golf on three private executive courses, tennis, pickleball, bocce, shuffleboard, fitness classes, entertainment, and an array of social activities. Residents also enjoy the lakeside lodge on Lake Tarpon, complete with a private boat ramp, fishing pier, and community pontoon boats, plus FREE RV and boat storage. The community is fully golf cart-friendly, making it easy to enjoy all the amenities and connect with neighbors. Ideally located near Gulf beaches, excellent dining and shopping, top-rated healthcare, major sports venues, two international airports, and a cruise port, this exceptional home offers the perfect combination of comfort, style, amenities, and the active Florida lifestyle. Don’t miss this rare opportunity in Highland Lakes—schedule your private showing today!

2336 Malcolm Drive, Palm Harbor

Listing courtesy of COLDWELL BANKER REALTY. 727-781-3700

$265,000

2 Beds ⋅ 2 Baths ⋅ W7889207 MLS

This charming single-story, block-built villa located in the desirable Highland Lakes 55+ community features 2 bedrooms, 2 bathrooms, an attached one-car garage, a full-size washer and dryer, and an easy-to-maintain homesite. Per the County, this property is located in a non-flood zone, and there is no CDD in this neighborhood. A standout 2026 upgrade is the replacement of all 8 windows with PGT impact-resistant, ENERGY STAR® windows, offering added storm protection, energy efficiency, and everyday peace of mind. This significant improvement combines durability and efficiency while providing a valuable upgrade for Florida living. Enjoy an exceptional sense of privacy with no neighbor on the right and no neighbor directly behind the property. The villa is surrounded by a huge yard, creating an expansive, open feel with plenty of green space all around. Enjoy the convenience of a thoughtfully sized floor plan that's ideal for year-round Florida living or a seasonal retreat. Nestled within the established Highland Lakes 55+ community in Palm Harbor, this home provides access to the active Florida lifestyle Highland Lakes is known for, with recreational and golf amenities nearby. The location puts you close to shopping, dining, medical facilities, recreation, and everything the Palm Harbor area has to offer, while the Gulf Coast's beautiful beaches and attractions are within easy reach. Whether you're looking to simplify your lifestyle, enjoy the Florida sunshine, or make Palm Harbor your home, 945 Madrid Drive offers an excellent opportunity to enjoy one of northern Pinellas County's established 55+ communities. Less than 30 minutes to St. Pete Beach, which was named the #1 Beach in America and the Fifth Best Beach in the World. Please view two videos: Tour 1 & Tour 2.

945 Madrid Drive, Palm Harbor

Listing courtesy of KELLER WILLIAMS REALTY- PALM HARBOR. 727-772-0772

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