Leesburg Homes with Trail(s) Amenities

Leesburg Homes with Trail(s) Amenities

Welcome to Leesburg, Florida, a charming city nestled in the heart of Lake County, where Southern hospitality meets stunning natural beauty. Known for its picturesque lakes and lush landscapes, Leesburg offers a delightful blend of small-town charm and modern convenience. With a rich history dating back to the 1800s, the city boasts a vibrant downtown area filled with unique shops, delightful eateries, and a variety of cultural events throughout the year.

One of the standout features of Leesburg is its commitment to outdoor living, particularly for those who appreciate an active lifestyle. Homes in this area often come with access to beautiful trails, perfect for walking, jogging, or biking. Imagine waking up each morning to the sound of nature and stepping outside your door to explore miles of scenic paths that wind through the stunning landscapes of Lake County. Whether you’re a seasoned outdoor enthusiast or simply enjoy a leisurely stroll, the trails in Leesburg offer something for everyone.

The community is also known for its friendly atmosphere, making it easy to connect with neighbors and participate in local events. From farmers' markets to art festivals, there’s always something happening in Leesburg that brings residents together.

With a variety of homes available, many of which feature trail amenities, Leesburg is the perfect place for those looking to embrace a lifestyle filled with adventure and community spirit. Discover your dream home in this enchanting city, where nature and community blend seamlessly!

Newest Leesburg Homes with Trail(s) Amenities

26949 Racquet Circle, Leesburg
$329,900
3 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 03 Tr A-G SubDv. ⋅ 34748 Zip Code
IMMACULATELY MAINTAINED 3-bedroom home in the sought-after GATED community of Highland Lakes. Beautifully UPDATED KITCHEN with dinette space OVER-LOOKING GREENSPACE/CONSERVATION area beyond. NO REAR NEIGHBORS and a peaceful setting with privacy. GRANITE countertops | Island | Subway tile backsplash | Stainless Steel appliances including natural gas range | re-faced cabinetry | NEW Luxury Vinyl Plank flooring (2026). INTERIOR LAUNDRY ROOM with tile flooring and ample cabinetry for additional storage space, includes NEW washer and gas dryer | SPLIT FLOORPLAN | Living and Dining combination | Family Room | Double Florida Room with heat and air wall unit, over-looks serene backyard and conservation land | Whole-house water purification system through Kinetico | ROOF 2016 | HVAC 2016 | Water Heater 2019 | UPDATED electrical (Siemens). Highland Lakes is a gated 55+ community situated in Central Florida just south of Leesburg & offers residents the following amenities: Recreational Clubhouse with two swimming pools; indoor (heated) & outdoor, a softball field complete with concession stand, an indoor arena with a stage for comm. events, complete kitchen, billiard/ping pong rm., 4 tennis courts (2 courts are lighted), 1 indoor tennis court, 8 lighted shuffle board courts, bocce ball courts, 2 outdoor and 4 indoor pickleball courts, 7 horseshoe pits, covered picnic pavilion with picnic tables & grills to barbeque, library, meeting/card room, exercise room/fitness, craft room, golf driving range, RV/boat storage (included in HOA) & has 260 spaces on a secured lot (fenced & lockable), a Craftsmen building/woodworking shop (homeowners can join the club for only $12 annually and use any/all tools available), there's also a Nature Trail within the community & seven lakes scattered throughout Highland Lakes; 4 are used by residents for catch & release fishing! Don't wait............. call now to schedule your private tour!

26949 Racquet Circle, Leesburg

109 Camellia Trail, Leesburg
$129,900
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Tucked near the Hawthorne Clubhouse, this charming two-bedroom, two-bath retreat offers a welcoming blend of comfort, style, and relaxed Florida living. With attractive vinyl siding, stone-accented landscaping, a long-paved driveway, and a charming picket fence, the home welcomes you with warmth and curb appeal from the very first glance. Step inside to discover a light-filled, coastal-inspired interior that captures the relaxed spirit of the Florida lifestyle. Soft, soothing colors and light-toned vinyl plank flooring create a seamless flow throughout, while reinforced subfloors provide added peace of mind. The atmosphere is bright, comfortable, and effortlessly inviting. The Florida room is a standout feature, offering a sunlit space to savor morning coffee, enjoy a good book, or unwind at the end of the day. Updated windows fill the room with natural light, making it a favorite place to relax and enjoy the easygoing pace of home. Thoughtful updates throughout reflect a true sense of care and pride of ownership. The 2023 HVAC system features a smart touchscreen thermostat for convenient climate control. The 2008 metal roof has been consistently serviced by the same trusted professional, while a 2022 interior electrical panel, the completely re-piped plumbing system, a newer water heater 2018, and new ceiling fans and light fixtures add comfort and convenience. Much of the important work has already been taken care of, allowing you to settle in and enjoy. The kitchen blends style and function with new quartz countertops and a tiled backsplash that adds timeless appeal. Both bathrooms have been refreshed with new quartz countertops, vanities, and medicine cabinets, creating a clean, updated look. The primary suite offers a modern touch with a sliding barn door leading to a walk-in shower, while the guest bathroom features a relaxing tub, ideal for everyday comfort and visiting friends or family. Additional thoughtful details include new cabinet and closet doors, dual storage spaces, a practical utility area, and a separate laundry room. Best of all, this home comes fully furnished, making your transition easy and giving you more time to enjoy the lifestyle you've been looking forward to. Warm, welcoming, and thoughtfully updated, this charming retreat is ready for its next chapter, and ready for you to feel right at home.................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.

109 Camellia Trail, Leesburg

5853 Princess Caroline Place, Leesburg
$284,999
2 Beds ⋅ 2 Baths ⋅ Royal Highlands Ph 01b SubDv. ⋅ 34748 Zip Code
Welcome to one of Royal Highlands’ most darling homes! Perfectly sized at 1,409 square feet under air, this two-bedroom, two-bath Onyx model offers effortless Florida living with a warm, inviting feel. Set on a gorgeous conservation lot, the home provides a front-row seat to native birds and peaceful natural views. Step through the sliding doors to the outdoor paver patio—an ideal place to relax, entertain, or enjoy your morning coffee. New living-room shades add comfort and style. This wonderfully move-in ready property with an optional nearly furnished consideration, this home feels as though it came straight from a Tommy Bahama catalog. Major improvements include a 2018 HVAC system and roof, 2019 windows, and a 2023 water heater. Inside, you’ll appreciate newly installed laminate wood flooring, fresh paint, plantation shutters, an updated primary bath with a glass-enclosed shower, and an updated guest-bath vanity. Additional features include a new garbage disposal, hurricane-tinted protection and privacy glass, as well as an updated backflow and irrigation. The immaculate garage is clean as a whistle and features a new epoxy floor, a newly finished driveway, new washer and dryer appliances, attic storage, a utility sink, and convenient side-yard access. Fresh exterior paint, block-and-stucco construction, and thoughtful updates throughout make this Pringle-built home an exceptional find. The kitchen features granite countertops, Shaker cabinets, and stainless appliances, including a gas range! Royal Highlands is a gated 55+ golf community featuring an 18-hole senior course, a full-service restaurant, courts, clubs, activities, and a large event center for entertainment, dances, and community functions. Residents also enjoy a fitness center, two pools, a library, billiards, and craft rooms. Located approximately 40 minutes from Orlando International Airport, Disney, and Orlando attractions, the community is also convenient to The Villages town squares, historic districts, shopping, restaurants, and both Florida coasts. Come tour this charming home today and discover the Royal Highlands lifestyle!

5853 Princess Caroline Place, Leesburg

353 Hawthorne Boulevard, Leesburg
$95,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Welcome to this furnished 2-bedroom, 2-bath home located on Hawthorne Boulevard in the desirable 55+ community of Hawthorne at Leesburg! Nicely landscaped and well-maintained, this home features numerous updates, including new laminate flooring, updated windows, a new front door, updated electrical panel, and a roof-over. The kitchen offers new countertops and a newer stove, while the primary bedroom features a new ceiling fan. Additional improvements include a three-year-old HVAC system and all-new ductwork. Enjoy the Florida room under heat and air, providing comfortable year-round living space. A convenient laundry room/workshop offers additional storage and workspace. Move right in and start enjoying Hawthorne's fantastic amenities and active lifestyle! Hawthorne at Leesburg is a vibrant 55+ community that blends comfort, convenience, and affordability. For just $397 a month, residents enjoy a maintenance-free lifestyle that includes water, sewer, lawn care, emergency services, and access to a wealth of resort-style amenities plus secure RV and boat storage. The expansive clubhouse is the social hub of the community, offering over 100 organized activities, a welcoming lounge, card rooms, billiards, a fitness center, a library, and a fine arts studio. A dedicated program coordinator ensures there’s always something fun and engaging on the calendar. For those who love the water, the private marina offers 120 boat slips with direct access to the beautiful Harris Chain of Lakes. Safety and peace of mind come standard, thanks to a 24/7 on-site team of state-certified firefighter/EMTs, emergency vehicles, and in-home emergency response buttons. Surrounded by natural beauty, the community features scenic walking trails, serene lake views, and plenty of opportunities for fishing and boating. The golf cart-friendly streets make it easy to explore nearby shopping, dining, and medical facilities. With a sparkling pool, endless recreational options, and a warm, welcoming atmosphere, Hawthorne at Leesburg isn’t just a place to live it’s a lifestyle. Schedule your showing today and discover the perfect blend of comfort, community, and convenience.

353 Hawthorne Boulevard, Leesburg

131 Bougainvillea Drive, Leesburg
$152,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Private Nature Retreat with Beautiful Landscaping & Extensive Updates! Enjoy peaceful living on a private, beautifully landscaped lot backing up to mature trees and tranquil wooded views. Relax on the back porch deck with retractable awning, entertain outdoors, or admire the long, decoratively painted driveway. Exterior features include vinyl siding, an aluminum roof, and a carport with Florida roof (2007). Inside, discover spacious bedrooms, seamless luxury vinyl tile flooring with no transitions, and numerous thoughtful updates. Subfloors have been repaired and verified sound, with new vapor barriers and insulation in 2025. Upgraded single-pane windows add to the improvements. The inviting kitchen features beautiful countertops, solid wood cabinetry (2021), backsplash, deep sink, and convenient pull-out shelving. Stainless steel appliances were installed in 2021, including a convection range with air-fryer capability, and the refrigerator was replaced in 2022. Both bathrooms have appealing upgrades. The primary bath features a walk-in shower, while the guest bath boasts granite countertops, new cabinetry, and a beautiful tiled, enclosed walk-in shower. Raised toilets and new ventilation fans (2025) add comfort and convenience. Additional interior updates include new interior doors, ceiling fans, light fixtures, upgraded wooden closet doors, and new dressers in the guest bedroom. Major improvements include HVAC (2020), water heater (2022), vapor barriers and insulation (2025), underground irrigation and underground ventilation fans (2025), and a tie-down system inspected in 2021. The carport and Florida roof date to 2007. With its beautiful landscaping, private wooded setting, spacious bedrooms, inviting outdoor living area, and extensive updates, this home offers a wonderful opportunity to enjoy comfort, privacy, and the beauty of nature!.............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.

131 Bougainvillea Drive, Leesburg

25233 Lost Oak Circle, Leesburg
$320,000
3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Hidden Oak Village SubDv. ⋅ 34748 Zip Code
Welcome to refined Florida living in the Plantation at Leesburg, a guard-gated community with 24/7 security where an active lifestyle, golf course scenery, and thoughtful home upgrades come together. Ideally positioned within the community—close to activities yet quietly set back—this well-cared-for 3-bedroom, 2-bath home offers peaceful golf course views and a private outdoor setting designed for year-round enjoyment. Inside, the home features a bright, open living and dining layout complemented by recent improvements throughout. The kitchen features custom cabinets, a custom backsplash, newer stainless steel appliances, a breakfast bar, and a dinette overlooking the golf course. The primary living areas and bedrooms are comfortably carpeted, while the kitchen, laundry room, and front entry feature luxury vinyl plank flooring. The spacious primary suite offers backyard views and an updated ensuite with a refreshed walk in shower, fixtures, and dual vanities. Step outside to the enclosed lanai, enhanced with new vertical blinds, window and frame repairs, thresholds, and its own air conditioning, allowing you to enjoy sunsets, wildlife, and golf course views in comfort. Additional updates include plantation shutters, a Bryant HVAC system installed in 2022, refreshed landscaping with sod, plants, edging, and brickwork, and a whole-house water filtration system. Residents of the Plantation at Leesburg enjoy a vibrant 55+ lifestyle with two championship golf courses, three clubhouses, heated pools, tennis and pickleball courts, walking trails, and a full calendar of clubs and social events, all conveniently located near shopping, dining, medical facilities, and major roadways—offering the lifestyle you’ve been waiting for in a move-in-ready home.

25233 Lost Oak Circle, Leesburg

101 Mandarin Cove, Leesburg
$129,900
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Welcome to this charming, furnished 2-bedroom, 2-bath home nestled on a quiet cul-de-sac in the desirable 55+ community of Hawthorne at Leesburg! This well-maintained home features tile and laminate flooring, six-panel doors, some updated double-pane windows, and a convenient Jack-and-Jill guest bathroom. The Florida room is equipped with heat and air, providing additional space to relax or entertain year-round. A standout feature is the whole-home generator, just three years old, offering added peace of mind. Additional highlights include a rubber roof-over, a 2012 HVAC system reported to be running great, a laundry area with utility sink, and a separate workshop/storage room. Outside, enjoy attractive landscaping and an extra-long golf cart parking pad with awning. Located in a resident-owned, gated community offering a private marina with access to the Harris Chain of Lakes, swimming pools, clubhouse, fitness center, and numerous social activities. This furnished home is ready for you to move in and start enjoying the Florida lifestyle! Hawthorne at Leesburg is a vibrant 55+ community that blends comfort, convenience, and affordability. For just $397 a month, residents enjoy a maintenance-free lifestyle that includes water, sewer, lawn care, emergency services, and access to a wealth of resort-style amenities plus secure RV and boat storage. The expansive clubhouse is the social hub of the community, offering over 100 organized activities, a welcoming lounge, card rooms, billiards, a fitness center, a library, and a fine arts studio. A dedicated program coordinator ensures there’s always something fun and engaging on the calendar. For those who love the water, the private marina offers 120 boat slips with direct access to the beautiful Harris Chain of Lakes. Safety and peace of mind come standard, thanks to a 24/7 on-site team of state-certified firefighter/EMTs, emergency vehicles, and in-home emergency response buttons. Surrounded by natural beauty, the community features scenic walking trails, serene lake views, and plenty of opportunities for fishing and boating. The golf cart-friendly streets make it easy to explore nearby shopping, dining, and medical facilities. With a sparkling pool, endless recreational options, and a warm, welcoming atmosphere, Hawthorne at Leesburg isn’t just a place to live it’s a lifestyle. Schedule your showing today and discover the perfect blend of comfort, community, and convenience.

101 Mandarin Cove, Leesburg

120 Camellia Trail, Leesburg
$109,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Fully Furnished Florida Home with Bonus Golf Cart! Welcome to this inviting, fully furnished home offering comfort, spacious living areas, and plenty of extras! The welcoming Florida room serves as the main entry into the home, creating a warm first impression and a relaxing space to greet guests or enjoy the Florida lifestyle. Best of all, the home comes with a bonus golf cart and sleeper sofa, making it even more convenient and ready to enjoy. The spacious living room and dining room provide plenty of room for entertaining, with built-in display cabinets adding charm and character. The fully equipped kitchen features additional built-in cabinets and shelving, offering extra storage and functionality for everyday living. Both bedrooms are generously sized and feature walk-in closets plus additional clothes closets, providing excellent storage space. The primary bathroom includes a walk-in shower, while the guest bathroom features a bathtub. Enjoy the outdoors in the spacious, enclosed screened side porch, conveniently accessible from the kitchen and connected to the carport. Parking is a breeze with a wide, expanded carport accommodating two vehicles, along with a separate covered golf cart pad. Additional conveniences include an extended utility room with a washer and dryer (2021), with direct access from the primary bedroom. Beautiful linoleum flooring and new doors add to the home's appeal. The HVAC system was updated in 2018, and the water heater dates to 2014. Upgraded single-pane windows complete the home's features. Come enjoy the comfort, convenience, and relaxed Florida lifestyle in this inviting home! With furnishings included, a well-equipped kitchen, generous living spaces, excellent storage, and parking for both vehicles and a golf cart, this home is ready for its next owner to move in and make it their own................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.

120 Camellia Trail, Leesburg

6121 Hunters Ridge Avenue, Leesburg
$400,000
4 Beds ⋅ 2 Baths ⋅ Legacy Of Leesburg SubDv. ⋅ 34748 Zip Code
FABULOUS 4-BEDROOM, 2-BATH LANGLEY II MODEL WITH LAGOON-STYLE POOL AND WATER VIEWS! Experience the ultimate Florida lifestyle in this impressive home featuring a SOLAR-HEATED SALTWATER POOL, HOT TUB, and TRANQUIL WATER VIEWS! Located in the highly sought-after 55+ community of Legacy of Leesburg, this property is surrounded by LUSH, MATURE LANDSCAPING, FRUIT TREES, and a SERENE POND BACKDROP. A screened front entry with an extended birdcage welcomes you into a light-filled interior, where your eye is immediately drawn through the glass sliders to a PRIVATE TROPICAL GARDEN SANCTUARY. Monarch butterflies, the soothing sounds of the pool’s waterfall, and birdsong create a peaceful retreat. Front and rear screened birdcages and a GLASS-ENCLOSED LANAI offer inviting indoor-outdoor living. A leaded-glass front door with sidelight opens to an airy, open-concept design featuring abundant windows, sliding glass doors, SOARING VAULTED CEILINGS, and beautiful tile plank flooring. The kitchen features wood cabinetry, Corian countertops, stainless steel appliances, a pantry, eat-in bar, and dinette. The living room opens through three-panel sliders to a 144-SQ-FT ENCLOSED TILE LANAI with vaulted ceilings. The primary suite offers lanai access, a walk-in closet, dual sinks, a soaking tub, a tiled walk-in shower, and a linen closet. A split floor plan provides a private guest wing with two bedrooms and a full bath. Bedroom 3 enjoys a large window overlooking the pool and waterfall. The FOURTH BEDROOM, with double French-door entry, tile plank flooring, a three-panel picture window, and a built-in closet, is ideal for a HOME OFFICE OR DEN. Additional features include an interior laundry room with shelving and an EXTRA-DEEP 21' X 25' GARAGE with a whole-house Nova water filtration system. DON’T MISS THIS OPPORTUNITY TO ENJOY YOUR OWN PRIVATE TROPICAL RETREAT! Legacy of Leesburg is an upscale 55+ community offering a nature-inspired setting with miles of walking trails and approximately half its acreage devoted to wildlife conservation areas, wetlands, and a bird refuge. Amenities include a resort-style pool and spa, fitness center, library, computer room, tennis, bocce, pickleball, horseshoes, shuffleboard, softball, and a variety of active social clubs and classes. The HOA includes lawn care, cable TV, internet, and on-site RV storage. Residents can stay informed through a dedicated community TV channel and the private “Legacy Neighbors” website. Conveniently located near Highway 27, the community offers easy access to dining, banking, medical facilities, golf courses, and more. WATCH OUR WALKTHROUGH VIDEO AND CALL TODAY TO SCHEDULE YOUR PRIVATE SHOWING!

6121 Hunters Ridge Avenue, Leesburg

21113 Edinborough Place, Leesburg
$389,999
3 Beds ⋅ 3 Baths ⋅ Royal Highlands Ph 01a SubDv. ⋅ 34748 Zip Code
Virtually Staged. Welcome to this modified and expanded three-bedroom, three-bath Majestic model in Royal Highlands, an active 55+ golf and pet-friendly community where HOA services include cable and internet. Offering 2,512 square feet under air, this flexible home has space for today’s lifestyle—whether you need a home office, game room, dedicated music room, or private suite with its own bathroom. Set along the 14th fairway of the Monarch Golf Course, the home features a screened lanai with western exposure and breathtaking sunset views. Inside, enjoy vaulted and tray ceilings, spacious rooms, casual and formal dining areas, a split-bedroom floor plan, interior laundry, abundant closets, and generous storage. The oversized garage can also accommodate a golf cart. Recent improvements include a brand-new 2026 roof with an updated Low-E glass skylight, fresh paint, exterior power washing, a new electric range, granite counters and updated sink, plantation shutters, and pet-friendly laminate flooring. A 2020 water heater adds peace of mind. Professionally trimmed oak trees, colorful wildflowers, and inviting curb appeal complete the setting, while the premium location keeps you close to community amenities. Royal Highlands offers 18 holes of golf, a driving range, an on-site restaurant, two pools, a fitness center, and a great hall hosting theater productions, live entertainment, and dancing. Residents can also enjoy courts, crafts, a kiln, a library, and more. Schedule your private tour today and discover the space, views, and active lifestyle this exceptional home has to offer!

21113 Edinborough Place, Leesburg

Start Your Search

How much is your home worth?

Get instant property value now!