Leesburg Homes under $500,000

Leesburg Homes under $500,000

Welcome to Leesburg, Florida—a charming city nestled in the heart of Lake County! Known for its picturesque lakes and vibrant community, Leesburg offers a perfect blend of small-town charm and modern amenities. With a rich history dating back to the late 1800s, this delightful city is surrounded by natural beauty, making it an ideal location for those who appreciate outdoor activities, including fishing, boating, and hiking.

One of the standout features of Leesburg is its affordability, particularly in the housing market. For homebuyers seeking a budget-friendly option, there are numerous homes available for under $500,000. This makes Leesburg an attractive choice for families, retirees, and first-time buyers alike. From cozy single-family homes to charming townhouses, the diverse selection of properties ensures that there is something to suit every taste and lifestyle.

In addition to its affordable housing, Leesburg boasts an array of amenities, including shopping centers, restaurants, and recreational facilities. The city's vibrant downtown area is home to a variety of local boutiques and eateries, perfect for a leisurely stroll or a night out. For those who enjoy cultural experiences, the annual Leesburg Bikefest and various art festivals offer plenty of opportunities to engage with the community.

With its friendly atmosphere, beautiful surroundings, and affordable housing options, Leesburg is not just a place to live; it’s a place to thrive. Come explore the possibilities and find your dream home in this delightful Florida gem!

Newest Leesburg Homes under $500,000

3813 Arbordale Court, Leesburg
$445,000
3 Beds ⋅ 4 Baths ⋅ Plantation At Leesburg Arbordale Village SubDv. ⋅ 34748 Zip Code
ROOF 2026 | WATER HEATER 2026 | GENERAC GENERATOR & LP TANKS 2025 | WINDOWS Insulated Low E with Lifetime Transferable Warranty 2017 | Spray Foam Attic Insulation 2011. This POOL home is move-in ready with an expansive floor plan which includes a Living Room, Family Room w/Wine Bar, Den and a cozy Breakfast Nook off of the spacious Kitchen. This Split Plan home features 3 Bedrooms, 3 Private Baths, and a Half-Bath off of the Living Room, Dining Room and Den, which offers comfortability for family and guests. The covered Florida Room features sliding vinyl windows/doors which open for access to the 24’ x 46’ Screen Enclosure over the Patio and Pool. Mature landscaping offers privacy for the Pool Area. The Generac Generator, two 120-gallon propane tanks and Automatic Transfer Switch activates when it detects power loss, and moves the home’s circuits over to generator power. When grid power returns, the Automatic Transfer Switch moves the home back to the utility, and the generator powers down, returning to standby until the next outage. This home is on a quiet cul-de-sac street, but convenient to all the community’s amenities. The Plantation at Leesburg, situated in Central Florida, is a well-established, access-controlled, 55-plus community that offers 3 fully staffed activity centers equipped with heated pools and spas, fitness facilities, two 18-hole golf courses, a driving range & putting green, Restaurant & Tavern, Pro Shop, woodworking shop, optional RV & Boat Storage, courts for tennis & pickleball, and a variety of activities. Only a short drive to main highways, shopping, health care facilities, attractions and beaches. Equal Opportunity Housing.

3813 Arbordale Court, Leesburg
127 Westwood Drive, Leesburg
$143,000
2 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph 01a SubDv. ⋅ 34748 Zip Code
WELCOME TO PENNBROOKE FAIRWAYS, WHERE EVERY DAY FEELS LIKE A VACATION! Discover comfortable, low-maintenance living in this sought-after, manned-gated 55+ golf community, conveniently located near The Villages! This lovingly maintained 1990 double-wide manufactured home offers 2 bedrooms, 2 bathrooms, and 1,086 square feet of inviting living space, along with additional areas designed for relaxation and entertaining. Step inside to discover a spacious GREAT ROOM with plenty of room to gather with friends and family or simply unwind at the end of the day. The kitchen features an adjoining dining area, creating a comfortable space for everyday meals and conversation. The primary bedroom offers the convenience of an ensuite bathroom, while the guest bedroom is situated near a separate full bathroom, providing comfort and privacy for visitors. An enclosed front room adds wonderful versatility and would make an ideal HOME OFFICE, hobby room, reading retreat, or additional sitting area. Prefer enjoying the Florida weather? The SIDE SCREENED PORCH provides another inviting spot to relax with your morning coffee or enjoy a peaceful afternoon. This home has been well cared for, with valuable improvements that include a NEW HVAC SYSTEM IN 2022 and UPDATED FLOORING in the kitchen and bathroom. But the appeal doesn't stop at the front door! PENNBROOKE FAIRWAYS OFFERS AN EXCEPTIONAL ACTIVE-ADULT LIFESTYLE with an impressive selection of recreational opportunities, social activities, and community amenities. Golf enthusiasts will appreciate THREE 9-HOLE GOLF COURSES, including two executive courses and one regulation-length nine-hole course. Golf memberships and greens fees are available separately and are not included in the HOA fee. Residents can also enjoy a fitness center, pool and spa, clubhouse, activity center, library, card and puzzle room, tennis and pickleball courts, shuffleboard, bocce ball, cornhole, horseshoe pits, fishing ponds, softball field, and community garden. With numerous clubs, organized activities, and special-interest groups, there are plenty of opportunities to stay active, meet neighbors, and make new friends. After a round of golf or an afternoon of activities, stop by THE GRILLE RESTAURANT for a bite to eat without leaving the community! Additional conveniences include RV AND BOAT STORAGE, while the HOA fee includes CABLE, INTERNET, AND LAWN CARE, allowing you to spend less time on maintenance and more time enjoying everything this wonderful community has to offer. Ideally situated near THE VILLAGES, with its extensive shopping, dining, entertainment, and medical facilities, Pennbrooke also offers convenient access to Orlando, approximately an hour away, and Florida's beautiful Atlantic and Gulf Coast beaches, each approximately 1.5 hours away. Whether you're searching for a full-time Florida residence or a seasonal retreat, this well-maintained home offers a wonderful opportunity to enjoy an active, welcoming community with amenities right outside your door. SCHEDULE YOUR PRIVATE SHOWING TODAY AND DISCOVER WHY SO MANY LOVE CALLING PENNBROOKE FAIRWAYS HOME! All information deemed reliable but must be verified by buyers. All room measurements are approximate and must be also verified by buyers.

127 Westwood Drive, Leesburg
26707 Cash Court, Leesburg
$234,900
2 Beds ⋅ 2 Baths ⋅ Highland Lakes SubDv. ⋅ 34748 Zip Code
Come and enjoy this low-maintenance Villa with 2 Master Suites, with the living area between these rooms for privacy. The roof was recently installed. The kitchen has a breakfast nook, an under-sink water filter, an electric range, a microwave hood, a closet pantry, and opens over a breakfast bar to the dining/living area. It boasts cathedral ceilings and plant shelves with a feeling of spaciousness. The living area opens through sliders to a screened lanai that overlooks a green lawn and conservation area, where you will enjoy watching birds and other wildlife. The garage has an enclosed storage area, a laundry area, and a unique garage door screen. A/C: July 2010. Dues include lawn maintenance, irrigation maintenance, water, termite bond, and more. This community offers a huge clubhouse, indoor & outdoor pools, mega sport courts, craft barn, and free RV and boat storage, plus numerous planned activities and clubs. Professional/Medical offices are at the front of the community. Located just 1 mile from banks, RX, groceries, restaurants, etc., and just 3 miles to public ramps into Lake Harris.

26707 Cash Court, Leesburg
1807 High Street, Leesburg
$238,000
3 Beds ⋅ 2 Baths ⋅ Leesburg Oak Crest SubDv. ⋅ 34748 Zip Code
This is a true gem with unmatched potential! Located in the heart of Leesburg, Florida, this 3-bedroom, 2-bathroom home sits close to downtown shopping, parks, and dining, offering incredible potential for your next portfolio addition or flip. This home needs cosmetic repairs and is a true investor's dream or if you are looking for something where you can bring your creativity and vision, this is it. The property features high-ticket structural upgrades already completed, including newer windows. The metal roof and brand -new electrical panel were both installed in 2019.Inspection sticker and permit number on Panel.

1807 High Street, Leesburg
602 Old Colony Road, Leesburg
$117,000
3 Beds ⋅ 2 Baths ⋅ Coachwood Colony SubDv. ⋅ 34748 Zip Code
Welcome to this inviting three-bedroom, two-bath home on a nicely elevated corner lot in Leesburg, Florida. Step inside to find beautiful newer flooring that adds a fresh, updated feel throughout. The huge Florida room is a fantastic extension of living space, ideal for entertaining, relaxing, or enjoying your morning coffee with friends and family. Outside, you’ll appreciate the convenient carport, patio for outdoor enjoyment, and a utility shed for extra storage. With its spacious feel, flexible layout, and inviting indoor and outdoor areas, this property is ready to welcome its next owner. Convenient Leesburg location near shopping, dining, and daily essentials. Schedule your showing today and come see all it has waiting for you!! Come on Home!!

602 Old Colony Road, Leesburg
32928 Enchanted Oaks Lane, Leesburg
$239,900
2 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph 01k Unit 03 SubDv. ⋅ 34748 Zip Code
Welcome to 32928 Enchanted Oaks Lane, nestled on a quiet cul-de-sac and backing to a peaceful wooded area offering a private, tranquil setting in the highly desirable Pennbrooke Fairways, a gated 55+ golf community in Leesburg, Florida! This 2-bedroom, 2-bath home offers 1,687 square feet of living space, a versatile office or flex room with French doors, a spacious living room, and a separate dining area. The kitchen features original wood cabinetry, ample storage, and an adjoining dinette. The primary suite includes an en-suite bathroom with a walk-in closet, dual sinks, and a walk-in shower. Additional features include an inside laundry room, a two-car garage, and a screened rear patio overlooking a peaceful wooded backdrop with no immediate rear neighbors. A new shingle roof was installed in 2023. The home offers an excellent opportunity for buyers looking to make cosmetic improvements and add their personal touches. Now, let's talk about Pennbrooke Fairways! This established, resident-owned 55+ community offers 24-hour gated security, three nine-hole golf courses, two swimming pools, a fitness center, tennis and pickleball courts, softball, bocce ball, shuffleboard, numerous other recreational opportunities and a golf cart friendly community. Residents enjoy two recreation centers, including the Grand Hall and Activity Center, an on-site restaurant, and a full calendar of social clubs, activities, and special events. The HOA provides lawn maintenance, cable television, and access to numerous community amenities, helping residents enjoy a more relaxed, low-maintenance Florida lifestyle. Golf privileges and certain activities may involve additional fees. Enjoy convenient access to The Villages! Pennbrooke Fairways is ideally situated within a short drive of The Villages and its popular Brownwood Paddock Square, offering an exciting variety of restaurants, shopping, nightly live entertainment, and special events. Nearby shopping centers, grocery stores, medical facilities, and everyday conveniences add to the appeal of this desirable location. Whether enjoying the recreational opportunities within Pennbrooke Fairways or exploring the dining, entertainment, and attractions of nearby The Villages, residents can appreciate the best of both worlds—an active Florida lifestyle combined with the comfort and tranquility of an established residential community.

32928 Enchanted Oaks Lane, Leesburg
4753 Heron Run Circle, Leesburg
$239,900
2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Heron Run SubDv. ⋅ 34748 Zip Code
**WELCOME TO 4753 HERON RUN – YOUR FLORIDA LIFESTYLE AWAITS!** Welcome to The Plantation at Leesburg, a beautiful, gated 55+ community where every day feels like a vacation! Whether you are searching for a year-round residence or the perfect winter retreat, this is your opportunity to enjoy the sunshine and all that Central Florida has to offer. The Plantation at Leesburg offers an exceptional lifestyle with two golf courses, three clubhouses, three swimming pools, fitness centers, pickleball, tennis, softball, billiards, walking trails, and an abundance of clubs and activities. Take a ride in your golf cart to the community restaurant and lounge to enjoy great food, entertainment, and time with friends. Say goodbye to cold winters, snow, and ice, and say hello to sunny Florida living! Come discover why so many homeowners love calling The Plantation at Leesburg home. Enjoy an active lifestyle, wonderful neighbors, and endless opportunities to make lasting memories. **Come see what makes living at The Plantation at Leesburg so special!**

4753 Heron Run Circle, Leesburg
4109 Arlington Ridge Boulevard, Leesburg
$358,000
2 Beds ⋅ 2 Baths ⋅ Leesburg Arlington Ridge Ph 02 SubDv. ⋅ 34748 Zip Code
Welcome to Arlington Ridge, an active, Gated 55+ Golf Community in Leesburg, FL! You will enjoy this beautifully maintained home, offered PARTIALLY FURNISHED! This 2-BEDROOM, 2-BATH home with a versatile FLEX ROOM is situated along the 11th fairway of the Golf Course and showcases an OPEN-CONCEPT FLOOR PLAN, perfect for everyday living and entertaining. As you approach the charming SCREENED-IN FRONT PATIO, you will enter a welcoming, nicely sized FOYER. The spacious LIVING ROOM features STACKABLE SLIDING GLASS DOORS leading to the COVERED, SCREENED-IN LANAI, where you can enjoy beautiful GOLF COURSE VIEWS and the best of the Florida lifestyle. The well-appointed KITCHEN features abundant SOFT-CLOSE CABINETRY with PULL-OUT DRAWERS, QUARTZ COUNTERTOPS, BREAKFAST BAR SEATING, modern APPLIANCES, a PANTRY, and a DINETTE AREA filled with natural light. The SPLIT-BEDROOM FLOOR PLAN provides added privacy, while the spacious PRIMARY SUITE offers an EN SUITE BATHROOM featuring CORIAN DUAL SINKS, a ROMAN SHOWER, a large WALK-IN CLOSET with Two Doors, and a PRIVATE TOILET ROOM. The SECOND BEDROOM is conveniently located toward the front of the home near the GUEST BATHROOM. Just off the kitchen, you will find the FLEX ROOM and LAUNDRY ROOM, with convenient access to the GARAGE. The home is situated on an attractively LANDSCAPED LOT featuring DECORATIVE RIVER ROCKS, a KUMQUAT TREE, and a GUAVA TREE. This desirable GOLF COURSE COMMUNITY offers RESORT-STYLE AMENITIES, including POOLS, a FITNESS CENTER, TENNIS, a RESTAURANT, a THEATER, and numerous SOCIAL ACTIVITIES. The low HOA fee of just $128/month includes access to the AMENITIES, LAWN CUTTING, EDGING, and BLOWING, 200+ CABLE TV CHANNELS, HIGH-SPEED INTERNET, a WI-FI ROUTER to broadcast the signal throughout the home, and TWO DVRs to record your favorite shows. Additional Features include: Luxury vinyl plank (LVP) flooring extends throughout the home, providing a cohesive look and easy maintenance. Refrigerator (2025), Microwave (2020), Range with Double Ovens, Whole-House Water Softener and Purification System, Gas Hot Water Tank, Irrigation System, and Annual HVAC System Tune-Ups. Conveniently located near SHOPPING, RESTAURANTS, MEDICAL FACILITIES, and THE VILLAGES. THIS HOME IS READY TO WELCOME YOU! All information provided is believed to be true and accurate at the time of data entry but is not guaranteed.

4109 Arlington Ridge Boulevard, Leesburg
6316 Cedar Landing Circle, Leesburg
$409,990
4 Beds ⋅ 3 Baths ⋅ Cedar Landings SubDv. ⋅ 34748 Zip Code
Pre-Construction. To be built. Welcome to the Serena, where convenience meets comfort across two thoughtfully designed stories. This clever home puts the owner’s suite right where you want it – on the main level – while keeping three additional bedrooms tucked away upstairs. The heart of the home shines with 9’4 ceilings and an open layout that makes the kitchen, dining, and family areas feel like one gorgeous space. Speaking of the kitchen, it boasts a 10’6” island that’s ready for everything from breakfast rushes to holiday cookie baking. Upgrades like a wall oven and beverage center can turn this space into your culinary dream. Upstairs holds a special surprise – a bedroom that can become a second owner’s suite – hello, multi-generational living! The adaptable loft space is ready for whatever your family throws at it – from movie marathons to homework sessions. With walk-in closets in every bedroom and smart storage solutions throughout, the Serena keeps clutter at bay. Best of all, the wall of windows and sliding glass doors leading to your patio (or optional lanai) bring the outdoors in, making every day feel a bit more like vacation. Introducing Cedar Landings in Leesburg, Florida! Resort-Style amenities including a zero-entry pool with cabana, a dog park with separate spaces for small and large dogs, a playground, and a 1-acre multi-use green space. 2 miles to the Florida Turnpike, 20 miles to Mt. Dora & Winter Garden, 35 miles to Downtown Orlando, 10 miles to Main Street in Leesburg with local favorite restaurants including The Brick and Barrel Public House, Turners Kitchen, & Prime 3, and 2 miles to The Monarch at Royal Highlands Golf Course. Golfers can play this course and grab burgers and brews at the club's eatery. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Photos and/or renderings are for illustrative purposes only and may depict upgraded landscaping, elevations, decorative features, or optional upgrades that may not be included in the home offered. Prices, financing, promotion, and offers subject to change without notice. Promotions cannot be combined with any other offer. Ask the On-site Sales and Marketing Representative for details on promotions, concessions, or any other details.

6316 Cedar Landing Circle, Leesburg
7051 North Shore, Leesburg
$499,900
2 Beds ⋅ 2 Baths ⋅ Treasure Island Shores 1st Add SubDv. ⋅ 34788 Zip Code
*BALMY BREEZES*BLUE HERONS*BREATHTAKING SUNSETS* These are just a few of the things you'll enjoy when you make this your home! The LARGE waterfront, private access lot on Lake Griffin is a rare opportunity with endless possibilities. Your new lifestyle will include boating, fishing, and enjoying gorgeous sunsets. The existing block and brick home offers a kitchen, dining room, living room with a fireplace, 2 bedrooms, 2 baths and a bonus room that is ideal for an office. A large Florida room has windows on 3 sides to take in the panoramic lake views. There is a 1 car attached garage, with a bathroom. This home is being sold as-is and offers a unique blank slate for your vision and renovations. The HVAC is approximately 3 years old. Septic system is less than 1 year old. There is an existing seawall that has withstood several hurricanes. The boat house and dock are in need of a total renovation. NO HOA and this small, friendly neighborhood, that feels like a step back in time, make this the ideal location for your dream home. Location is convenient to Leesburg, Eustis, Mount Dora and Tavares. BRING YOUR DREAMS AND VISION AND COME SEE THIS EXCEPTIONAL OPPORTUNITY TODAY!!!

7051 North Shore, Leesburg
208 Waterfront Drive, Leesburg
$89,900
2 Beds ⋅ 2 Baths ⋅ Brittany Estates SubDv. ⋅ 34748 Zip Code
Direct lakefront on the Harris Chain of Lakes in the sought after 55 + community of Brittany Estates! 2 bedrooms 1.5 baths with large Florida room and double carport. Large backyard with gorgeous view of Lake Griffin. As a share holder, you can enjoy, the clubhouse, marina,, fishing pier, and heated and screened pool. For just $160 a month water, sewer, lawn mowing, and trash service is included. The community is golf cart and pet friendly. Don't t miss out on this rare opportunity to enjoy the Florida Lifestyle!

208 Waterfront Drive, Leesburg
1713 Birchwood Circle, Leesburg
$289,000
4 Beds ⋅ 2 Baths ⋅ Leesburg Birchwood Sub SubDv. ⋅ 34748 Zip Code
Seller also selling four other duplexes (can be purchased as a package deal) 1715 Birchwood Cir, 1717 Birchwood Cir, 1108 Birchwood Ct and 907 Nebraska St all in Leesburg, FL. Great way to add to your portfolio and create instant cash flow! Don't miss out on this charming duplex with two 2bed/1bath units! This home boasts tile floors throughout and features ceiling fans in each bedroom and the living room for year-round comfort. You'll also enjoy a private parking space and additional storage with a closet for washer/dryer hookups. Schedule your private viewing today!

1713 Birchwood Circle, Leesburg
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