Leesburg Homes under $500,000

Leesburg Homes under $500,000

Welcome to Leesburg, Florida – a charming city nestled in the heart of Lake County, where picturesque landscapes and vibrant community life come together to create an idyllic living experience. Known for its rich history and warm southern hospitality, Leesburg offers residents a unique blend of small-town charm and modern amenities. With its beautiful lakes, lush parks, and bustling downtown area, this city is perfect for families, retirees, and everyone in between.

One of the most appealing aspects of Leesburg is its diverse real estate market, particularly for those seeking homes under $500,000. Here, you can find a variety of options that cater to different lifestyles and preferences. Whether you’re looking for a cozy single-family home, a spacious townhouse, or a charming bungalow, Leesburg has something for everyone. Many of these homes feature beautiful yards, inviting porches, and modern updates, making them perfect for both relaxation and entertaining.

In addition to affordable housing, Leesburg boasts an array of recreational activities. From boating and fishing on the Harris Chain of Lakes to exploring the scenic nature trails in local parks, outdoor enthusiasts will find plenty to keep them active. The city also hosts a variety of community events, farmers' markets, and cultural festivals that foster a strong sense of belonging among residents.

With its affordable homes, friendly atmosphere, and abundant recreational opportunities, Leesburg, Florida, is not just a place to live – it’s a place to thrive. Discover your dream home in this delightful city today!

Newest Leesburg Homes under $500,000

1518 Crest Avenue, Leesburg
$224,900
3 Beds ⋅ 2 Baths ⋅ Leesburg Oakhill Park SubDv. ⋅ 34748 Zip Code
Welcome home! This beautiful renovated 3-bedroom, 2-bathroom residence in Leesburg, Florida, offers a comfortable layout and elegant finishes throughout the home. This Seller used modern fixtures to include shaker style doors with new trim. This is a must see! Inside, you’ll find luxury vinyl flooring in the main living areas, along with ceramic tile in the kitchen and both bathrooms. The kitchen is designed for everyday living as well as hosting guests, featuring quartz countertops, built-in double ovens, an electric cooktop, and the added convenience of having gas service available for those who prefer cooking with gas.

1518 Crest Avenue, Leesburg
122 Tamarisk Way, Leesburg
$274,900
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
MORE PHOTOS COMING SOON! Welcome to this beautifully updated, move-in-ready home offering an exceptional combination of modern upgrades, thoughtful design, abundant storage, and water view! Every detail has been carefully considered to create a home that is as functional as it is inviting. The beautifully remodeled kitchen is sure to impress, featuring elegant quartz countertops, stainless steel appliances, custom cabinetry with convenient pull-out shelving, soft-close drawers, and stylish under-cabinet lighting. Additional touches include built-in USB outlets and a skylight that fills the space with natural light. Dimmer switches throughout the home allow you to create the perfect ambiance for any occasion. One of the most remarkable features of this property is the expansive bonus room, currently used as an art studio. Surrounded by panoramic windows overlooking a peaceful pond, this incredible space offers water views and endless possibilities! Whether you envision a creative studio, entertainment area, hobby room, or relaxing retreat, this is truly a space you must experience in person. An adjoining office provides additional versatility and leads to an impressive custom-designed storage area featuring extensive shelving and large, covered storage containers. For those who appreciate a dedicated workspace, the oversized 14' x 32' workshop is an absolute standout! Equipped with heating and air conditioning, a utility sink, and an abundance of thoughtfully arranged storage, this exceptional space is ideal for woodworking, hobbies, projects, or simply keeping everything organized. The spacious primary bedroom features distinctive custom ceiling details and generous closet space, while the beautifully updated en-suite bathroom offers a walk-in shower and contemporary finishes. The guest bedroom includes additional custom storage above the closet, maximizing every inch of available space. Both bathrooms feature attractive granite countertops and tile flooring, with a skylight in the guest bathroom providing additional natural light. Additional improvements include a NEW ROOF IN 2025, HVAC SYSTEM INSTALLED IN 2020, WATER HEATER REPLACED IN 2017, and attractive, low-maintenance laminate and vinyl flooring. The numerous custom features and upgrades throughout reflect the care and attention the current owners have invested in making this home truly special. Located in the highly desirable Hawthorne at Leesburg, a gated, resident-owned cooperative 55+ waterfront community, you'll enjoy an active Florida lifestyle surrounded by beautifully maintained landscaping, scenic ponds, and illuminated fountains. Residents have access to an impressive clubhouse offering more than 100 activities, a fitness center, a swimming pool, and a private marina with 120 boat slips providing access to the Harris Chain of Lakes. The affordable $397 monthly maintenance fee includes water, sewer, lawn care, emergency services, and secure RV and boat storage. An especially valuable community feature is the on-site, 24/7 emergency response team staffed by state-certified firefighter/EMTs, along with in-home emergency alert buttons for added peace of mind. With its extensive upgrades, incredible storage, oversized workshop, and spectacular pond views, this one-of-a-kind home offers features you won't find in just any property. Schedule your private showing today and discover everything this exceptional home and community have to offer!

122 Tamarisk Way, Leesburg
31744 Boadwater Ave, Leesburg
$369,900
4 Beds ⋅ 3 Baths ⋅ Seasons At Park Hill SubDv. ⋅ 34748 Zip Code
MOTIVATED SELLER! Welcome to this spacious 4-bedroom, 3-bathroom home offering over 2,500 square feet of comfortable living space. Enjoy generously sized rooms, a spacious living area, and a versatile loft perfect for a home office, game room, or family retreat. Modern finishes include luxury vinyl tile flooring throughout and quartz countertops in the kitchen and all bathrooms. Additional features include an upstairs laundry room, a two-car garage, and a covered patio overlooking the vinyl-fenced backyard perfect for relaxing or entertaining. Conveniently located near shopping, restaurants, schools, medical facilities, Downtown Leesburg, Venetian Gardens, and the Harris Chain of Lakes, this home offers comfort and easy access to Florida's outdoor lifestyle. ***Perfect for FIRST TIME homebuyers or growing families! Schedule your private showing today!**

31744 Boadwater Ave, Leesburg
201 N East Street, Leesburg
$190,000
3 Beds ⋅ 1 Baths ⋅ Avalon Park Sub SubDv. ⋅ 34748 Zip Code
This 1940s bungalow-style single-family home features 3 bedrooms and 1 bathroom, situated on a spacious corner lot. This property offers a cozy, traditional layout with plenty of potential for additional updates. Located in the heart of Leesburg, this single-family home features a solid concrete block foundation and excellent construction. Ideal for first-time homebuyers or a great investment opportunity! This property offers a convenient location, with comfortable living space and a large screened-in front porch that provides the perfect spot to savor those summer breezes. Noteworthy features of this home include a unique outdoor square, two-toned rustic finish fire pit, ideal for gathering with friends and family for some outdoor fun! Enjoy the convenience of being a short distance to several public buildings, convenience stores, and parks. The property has some updates to include a new AC, and a prime location, this property is a must-see for anyone looking for a charming and affordable home in Leesburg.

201 N East Street, Leesburg
341 Ranchwood Drive, Leesburg
$319,000
3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph 01h SubDv. ⋅ 34748 Zip Code
Welcome home to 341 Ranchwood Drive, where privacy, flexibility, and the Pennbrooke Fairways lifestyle come together beautifully. Set against a peaceful, nature-filled backdrop, this thoughtfully maintained 3-bedroom, 2-bath home offers the kind of setting that makes it easy to forget how close you are to everything Central Florida has to offer. Step inside and you'll immediately appreciate a floor plan designed for comfortable Florida living. The main living spaces flow naturally together, while the split-bedroom design provides welcome separation between the primary suite and guest accommodations. An expansive 18' x 11' bonus area adds tremendous versatility—create a formal dining space, home office, reading room, hobby area, or simply additional room for entertaining. The primary suite offers a comfortable retreat with a generous walk-in closet and private bath featuring dual sinks and a walk-in shower. Two additional bedrooms provide plenty of space for visiting family and friends, an office, or whatever your next chapter requires. What makes this home particularly appealing is the combination of indoor comfort and outdoor living. A 9' x 17' screened lanai overlooks the home's private natural surroundings and creates an inviting spot to begin the morning with coffee or wind down at the end of the day. Just beyond it, the freshly refurbished open patio provides additional space for grilling, entertaining, or simply enjoying the Florida sunshine. The home has also seen substantial investment over the years, including a 2017 roof, 2017 windows and two sliding doors, added attic insulation in 2021, stainless-steel appliances in 2022, a new water heater and water softener in 2023, and a new HVAC system installed in April 2024 with a transferable warranty. Additional improvements include the lanai roof being re-shingled and the pavers resealed in 2024, along with painting of the front patio, garage, and porch in 2022. An oversized 2-car garage with dedicated golf cart access and a sliding screen adds even more functionality. Of course, buying in Pennbrooke Fairways is about more than the home. This gated 55+ community is built around an active Florida lifestyle, with golf, swimming pools, fitness facilities, pickleball, tennis, bocce ball, shuffleboard, cornhole, a restaurant, pro shop, Grand Hall, two recreation centers. The $265 monthly HOA fee includes cable, internet, lawn mowing and edging, plus boat and RV parking and storage. When you do decide to venture beyond the community, the location makes it easy. Lake Deaton Plaza—with Publix, Walgreens, dining and everyday conveniences—is just minutes away, while I-75, US-301 and The Villages are easily accessible. An evening of dining, shopping and live entertainment are just a short drive from home. 341 Ranchwood Drive isn't simply a place to live. It's an opportunity to have the privacy you want, the amenities you enjoy, and the freedom to make your next chapter in Florida exactly what you want it to be. WHO YOU WORK WITH TRULY MATTERS — LET US SHOW YOU WHY.

341 Ranchwood Drive, Leesburg
26717 Wetlands Way, Leesburg
$365,000
3 Beds ⋅ 3 Baths ⋅ Leesburg Legacy Leesburg Unit 06 SubDv. ⋅ 34748 Zip Code
The perfect forever home in an active senior community with all the amenities and clubs you could want. Enjoy tennis, pickleball, walking trails, a clubhouse, and more. This well-maintained home offers three full bedrooms plus a den/office/craft room, vaulted tray ceilings, and abundant kitchen cabinetry. Relax and enjoy the gorgeous view with easy living, lawn care included and room for your golf cart. FHA-insurable, subject to FHA appraisal. Qualifies for FHA $100 program and FHA 203(k) – contact your lender for details. Buyer selects Closing Agent. AS-IS only. Seller provides no guarantees, warranties, or repairs. Buyer must verify all information, including any measurements, possible violations, permits, HOA rules, zoning, etc.

26717 Wetlands Way, Leesburg
24907 Cranes Roost Circle, Leesburg
$375,000
3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Golfview SubDv. ⋅ 34748 Zip Code
ATTENTION: IF YOU DO NOT WANT EXTRA ROOM FOR VISITORS, OR AN UPGRADED HOME FOR ENTERTAINING, WITH A VIEW, OR THE HIGHEST PRICED HOME ON THE STREET THEN THIS HOME MAY NOT BE FOR YOU. BUT IF YOU WANT ALL THAT AND MORE ... Welcome to 24907 Cranes Roost Boulevard, a beautifully updated Seville model located in the desirable Golf View Village of Plantation at Leesburg. Set along the 15th fairway and overlooking the 16th tee of the Cranes Roost Golf Course, this home offers peaceful golf course views, extensive upgrades, and a low-maintenance lifestyle. This spacious home features 3 bedrooms, 2 bathrooms, plus a flexible den that can be used as an office, fitness room, hobby space, or additional sitting area. From the moment you arrive, the screened front entry and storm door create an inviting welcome. Inside, luxury vinyl plank flooring flows through the main living areas, complemented by updated finishes and thoughtful details throughout. The beautifully remodeled kitchen is a standout, featuring custom cabinetry, quartz countertops, double islands, upgraded pantry and closet doors, and LG stainless steel appliances. Custom remote-control blinds add both style and convenience. Both bathrooms have been completely renovated with updated vanities, fixtures, and finishes. The living area features an electric fireplace, with the original wood-burning fireplace located behind it, giving future owners additional options for creating a warm and inviting gathering space. The 2-car garage has been transformed into an impressive bonus area with insulation, updated flooring, overhead screen door, cabinetry, and a mini-split heating and cooling system. It offers a comfortable space for entertaining, hobbies, a workshop, or additional recreational use while maintaining the versatility of the garage. Outdoor living is just as appealing. The home features attractive low-maintenance landscaping with decorative curbing and stain-resistant rock. The Chattanooga stone and electric fireplace enhance the lanai. An additional BBQ patio provides the perfect spot for grilling, entertaining, or simply relaxing while enjoying the golf course setting. Major updates include a NEW ROOF and HVAC SYSTEM installed in 2022, providing added peace of mind. Golf View Village offers additional HOA-maintained benefits, including a PRIVATE COMMUNITY POOL, scheduled exterior pressure washing of the home, and lawn mowing, allowing residents more time to enjoy the Florida lifestyle. Plantation at Leesburg is a gated 55+ active community offering an impressive selection of amenities. Residents can enjoy two golf courses, three clubhouses, swimming pools, a hot tub, sauna, fitness centers, tennis, bocce ball, softball, walking trails, archery, RV storage, meeting and activity rooms, and a full calendar of clubs, social events, and planned activities. With its golf course setting, beautifully remodeled interior, extensive upgrades, and desirable Golf View Village location, this home offers an exceptional opportunity to enjoy comfortable, low-maintenance living in one of Leesburg's established active adult communities.

24907 Cranes Roost Circle, Leesburg
32930 Indian Woods Drive, Leesburg
$345,000
3 Beds ⋅ 2 Baths ⋅ Silver Lake Forest SubDv. ⋅ 34788 Zip Code
Virtually Staged. Welcome home! Check out this beautifully renovated 3-bedroom 2 bathroom with a 2-car garage single family home on a spacious corner lot! Featuring a BRAND-NEW ROOF and the seller will replace the HVAC prior to closing. As soon as you drive up to the property, you'll be greeted with the spacious large front yard & back yard. As soon as you walk into the home, you'll be greeted by high ceilings, new paint and luxury vinyl flooring throughout. This property boasts a spacious living room with sliding glass doors out to your backyard screened in patio! This home has a split floorplan with a large master suite, walk in closets and private master bathroom. The kitchen features plenty of cabinet and countertop space as well as an island, everything you need to bring out your inner chef! The kitchen island overlooks the dining room, making it effortless to host and entertain. Take full advantage of everything this property has to offer! Contact the listing agent today to schedule your showing.

32930 Indian Woods Drive, Leesburg
10381 Church Hammock Road, Leesburg
$375,000
4 Beds ⋅ 3 Baths ⋅ Silver Basin SubDv. ⋅ 34788 Zip Code
Welcome to this beautiful 4-bedroom, 3-bathroom home in Leesburg! Built in 2023, this single-story home offers approximately 2,077 square feet of living space with a bright, open layout designed for comfortable everyday living. The spacious kitchen features a large center island, ample cabinetry, and generous counter space, flowing into the main living and dining areas. Enjoy a modern interior, tile flooring, and a functional layout with plenty of room to relax or entertain. Don't miss the opportunity to make this inviting home your own!

10381 Church Hammock Road, Leesburg
355 Hawthorne Boulevard, Leesburg
$80,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Virtually Staged. A Home with Character, Possibility & Room to Make It Your Own. Please pardon the transition as the seller works through sorting, packing, and clearing the home for its next chapter. Beneath the boxes and belongings is a comfortable 2-bedroom, 2-bath home with plenty of possibilities and the opportunity for its new owner to bring their own vision to life. Set along Hawthorne Blvd with a beautiful tree-lined median, the setting has a welcoming, established feel. The home features vinyl siding, a screened back porch, and vinyl plank flooring added in 2026 in the living and dining areas. Both bedrooms are generously sized and include dual closets, making storage a standout feature. The primary suite includes a walk-in shower, while the Jack-and-Jill guest bath offers a traditional tub. The HVAC was replaced in 2014, adding to the home’s practical appeal. Whether you’re looking for a place to settle in, refresh over time, or create something that feels distinctly your own, this home offers a solid starting point in a lovely location. Come see the possibilities beyond the boxes and imagine what the next chapter could look like..............Hawthorne at Leesburg is an active, resident owned, 55+ cooperative, waterfront, gated community, with beautifully landscaped grounds, lakes with illuminated fountains and a relaxing and comfortable gazebo. The affordable monthly maintenance fee of $397 includes water, sewer, lawn mowing, private emergency services and storage space for recreational vehicles, boats, trailers and much more! The beautiful clubhouse is complete with a full-time program coordinator, more than 100 different activities and seating for 550. It has a hospitality lounge, card rooms, craft rooms, billiard room, fitness center, library, fine arts room and many more. There is excellent fishing, outdoor geo-thermally heated pool and two enclosed therapeutic pools. Hawthorne boasts a private marina monitored by an electronic security system with over 120 boat slips and access to the Harris Chain of Lakes and beyond.

355 Hawthorne Boulevard, Leesburg
410 Hawthorne Boulevard, Leesburg
$123,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg SubDv. ⋅ 34748 Zip Code
Welcome to 410 Hawthorne Boulevard in Hawthorne at Leesburg, Lake County's premier guard-gated 55+ community. This updated 2-bedroom, 2-bath home sits on a scenic boulevard with a landscaped median. It has 1,312 heated square feet and 1,698 total square feet, and the big ticket item upgrades are already done. A premium rubber membrane roof-over was added in 2017. It's rated ENERGY STAR by the U.S. Department of Energy and comes with a lifetime warranty. The added insulation helps the AC run more efficiently, cuts outside noise and stands up better to wind. ENERGY STAR dual-glazed windows run throughout the main house, except the kitchen and bathroom windows. The exterior was freshly painted in 2024, and new awnings were added in 2025. The home has an energy-efficient Carrier AC system (2017) with advanced R6 flex ductwork for better airflow. All of the original plumbing has been replaced, and the water heater was updated in 2025. The home has a 200-amp electrical service with an updated premium breaker panel that meets all current codes. Intermatic surge protection covers the whole house at the main breaker, with a second unit protecting the AC. This home has passed the pre listing 4-point inspection so it is ready and able to be insured. Inside, the home is carpet-free. Laminate flooring runs through every room, including both Florida rooms and the utility room, over a subfloor reinforced with plywood for extra durability. The kitchen has new waterproof flooring, stone wall covering below the cabinets and stainless steel appliances. It also has room for a full-size 30" refrigerator, a garbage disposal and an under-counter drinking water filter. The master bedroom is spacious and features a large walk-in closet plus a long wall closet and the guest bedroom is also large in size and also has a walk-in closet plus a wall closet. The remodeled guest bath has a full 5-foot tub with shower, an updated vanity and countertop, a Kohler sink and toilet, and AirStep vinyl flooring. Four more closets hold linens, pantry items, medicine and jackets. You can reach the laundry without going outside. The front Florida room is cooled by the home's central AC through floor ducts, so you can use it year-round for morning coffee or evening relaxing. A second enclosed Florida room at the carport has dual-glazed windows. Vertical blinds are included. Community amenities include a clubhouse, pool, fitness center, tennis, a marina, a boat ramp and access to the Harris Chain of Lakes. Also: service pets are welcome. It's golf-cart friendly and just minutes from shopping and dining in The Villages.

410 Hawthorne Boulevard, Leesburg
1145 Eagles Landing, Leesburg
$249,900
3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph 02s Lt S1 Orb 2145 Pg 1477 SubDv. ⋅ 34748 Zip Code
Virtually Staged. HOA includes grass cutting, Cable TV, Internet, 2 pools, 2 Recreation Centers, 3 9 hole golf courses, Restaurant, 100's of activities and Clubs to enjoy! Amenities in Pennbrooke Fairways includeVideo Tour of Pennbrooke Fairways: Welcome Center, On Site Hair Salon, Library, Fitness Center, Fitness Center Equipment Room, on Site Mail Room, Billiard Room, Activity Center, Activity Center Pool and Spa, Activity Center Kitchen, Card/Puzzle Room, Tennis/Pickle Ball Courts, Shuffleboard Courts, Bocce Ball Courts, Grand Hall Pool and Spa, Corn Hole, Horseshoe Pits, Fishing Ponds, Golf Club, Softball Field, Community Garden, Memory Garden and RV & Boat Storage. This home is on a quiet cul-de-sac with no rear neighbors other than nature. Price to sell!!

1145 Eagles Landing, Leesburg
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