Leesburg Homes with HOA

Leesburg Homes with HOA

Welcome to Leesburg, Florida – a charming city nestled in the heart of Lake County, where southern hospitality meets vibrant community living. Known for its picturesque landscapes and friendly atmosphere, Leesburg offers an idyllic setting for families, retirees, and anyone seeking a peaceful yet engaging lifestyle.

With its rich history and diverse culture, Leesburg boasts a variety of local attractions, from the historic downtown area filled with quaint shops and delightful eateries to the stunning waterfront parks along the beautiful Harris Chain of Lakes. Outdoor enthusiasts will appreciate the abundance of recreational activities available, including boating, fishing, and hiking, all set against the backdrop of Florida’s natural beauty.

For those considering a move to this enchanting city, Leesburg features a variety of homes, many of which are part of well-maintained communities with Homeowners Associations (HOA). These HOA communities offer a range of amenities designed to enhance your living experience, including community pools, fitness centers, and social clubs, fostering a strong sense of community among residents. The HOA also ensures that the neighborhoods remain beautifully landscaped and well-kept, providing a welcoming environment for all.

Whether you’re looking for a cozy single-family home or a spacious villa, Leesburg has something to suit every taste and budget. Embrace the charm and warmth of this delightful city, where the sun shines bright, and a vibrant community awaits you. Come discover your dream home in Leesburg – where every day feels like a vacation!

Newest Leesburg Homes with HOA

25247 Cranes Roost Circle, Leesburg
$244,900
2 Beds ⋅ 2 Baths ⋅ G5119329 MLS
Come and join in the fun in this snowbird friendly neighborhood. Yards are maintained by Golfview HOA. They also powers wash your house twice a year. This community also enjoys their private pool only available to Golfview residents. 2 bedrooms, plus den 2 car garage, front screened porch and back screened porch for relaxing on those warm Florida days. Don't relax too much because there is so much to do in this community. Driveway parties are especially popular. 36 holes of golf and friendly golfers to team up with. On site restaurant is a short golf cart drive away. Enjoy live music on the patio of the Oaks Grille or sing along to karaoke. 3 amenity centers await you with everything from bingo to craft fairs to fitness center, library, dances and 3 heated pools. It is time to join in the lifestyle of the Plantation at Leesburg, a premiere 55 plus guard gated community.

25247 Cranes Roost Circle, Leesburg
1019 Meadowbend Drive, Leesburg
$344,900
3 Beds ⋅ 2 Baths ⋅ G5119337 MLS
3 BEDROOMS | 2 BATHROOMS | BLOCK/STUCCO | PRIVACY IN BACK| ROOF (2023) | WATER HEATER 2022| STAINLESS STEEL APPLIANCES | THERMO PANE WINDOWS| Welcome home to this beautifully maintained custom home in Pennbrooke Fairways, one of Central Florida’s premier gated 55+ GOLF communities. From the moment you pull up, notice the lovely hardscape & updated landscaping as well as the painted driveway & sidewalk. This inviting residence offers privacy, generous living spaces, and the relaxed Florida lifestyle. Step through the elegant leaded-glass front door with side lites into a bright, open floor plan featuring beautiful laminate flooring in the main areas, high ceilings, Updated lighting, and a gorgeous oversized enclosed Florida room (10 x 28) overlooking the private back. The spacious family room flows into the Florida room, creating an ideal setting for everyday living, entertaining, and enjoying the private backyard. The kitchen features abundant cabinetry, stainless steel appliances, a breakfast nook, generous storage, and ample workspace. The thoughtfully designed floor plan includes a spacious primary suite with his and hers walk-in closets, a fully renovated bathroom featuring dual quartz vanities, private water closet and a custom shower that is sure to impress! The second bedroom and full bath/shower combo can easily function as a second primary suite. Additionally, a 3rd bedroom without a closet, featuring double doors can serve as a den or home office. The expansive Florida room overlooking the private backyard area is a true highlight, offering a peaceful setting to enjoy morning coffee, or entertain friends. Additional features include an interior laundry room with a stainless steel utility sink and cabinetry, an oversized two-car garage, a large paver patio area in back, R-38 insulation in home, R30 Insulation in Florida Room, New Carpet in bedrooms (2025) and mature landscaping. Pennbrooke Fairways features 27 holes of golf, a pro shop, an on-site restaurant, two recreation centers, swimming pools, a fitness center, and countless activities including pickleball, tennis, shuffleboard, softball, horseshoes, water volleyball, and cornhole. Conveniently located near shopping and dining and just 6 miles from The Villages' Brownwood Paddock Square, this home offers the perfect combination of comfort, convenience, and an active Florida lifestyle. Enjoy maintenance-free living with a low monthly HOA fee of just $265, which includes lawn care, high-speed internet, cable, and access to an outstanding selection of community amenities.

1019 Meadowbend Drive, Leesburg
4408 Bedford Way, Leesburg
$269,900
2 Beds ⋅ 2 Baths ⋅ G5119385 MLS
ASSUMABLE 3.5% FHA MORTGAGE!! MAINTENCE FREE Built in 2022 this home is extensively upgraded Custom Plantation shutters thru out, custom closet organization thru out including laundry room, 6 solar tubes electronically control for daylight, whole home water treatment system, under the sink 5 stage osmosis water treatment system, luxury vinyl flooring thru out, security system, gutters,14x5 extended rear patio, screened lanai, front entry storm door, upgraded landscaping,10 year parts and labor HVAC warranty, white shaker cabinetry, primary suite has custom walk in closet with built in drawers and shoe storage, walk in tiled shower with glass shower door. This home was thoughtfully upgraded and beautifully maintained. Every improvement, from custom closets to specialty lighting to premium outdoor enhancements have been completed so you can enjoy your retirement lifestyle. Arlington Ridge is a 55 plus golf course community rich in amenities to include, movie theater, on site restaurant, library, fitness center, heated pools, craft center and many clubs and organizations. HOA fee includes lawn and landscape maintenance, yard irrigation, roof replacement, exterior painting, cable tv and internet. FHA loan is assumable thru FHA qualification guidelines.

4408 Bedford Way, Leesburg
353 Hawthorne Boulevard, Leesburg
$95,000
2 Beds ⋅ 2 Baths ⋅ G5119387 MLS
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 ⋅ G5119353 MLS
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 offer 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
4704 River Ridge Drive, Leesburg
$389,000
3 Beds ⋅ 2 Baths ⋅ G5118948 MLS
WELCOME HOME TO THE PLANTATION AT LEESBURG! This exceptional golf course home was thoughtfully upgraded by owners who intended it to be their forever home, and it shows in every detail. Perfectly situated overlooking the 6th hole with no rear neighbors, this beautifully updated residence offers the ideal combination of comfort, efficiency, and resort-style living in one of Central Florida's most desirable 55+ communities. The heart of the home is a stunning renovated kitchen featuring updated cabinetry, granite countertops, modern fixtures, and newer appliances. Both bathrooms have been beautifully remodeled with granite countertops, updated fixtures, and walk-in showers, while the spacious primary suite offers dual closets, a garden tub, and a relaxing retreat at the end of the day. Major upgrades provide peace of mind for years to come, including a 2015 roof, new double-pane double-hung tilt-in windows, new sliding glass doors, replaced HVAC ductwork (2020), whole-house water softener system, recessed lighting throughout, and luxury vinyl flooring throughout the home. Step outside to the screened lanai featuring an insulated roof rated for winds up to 125 mph and enjoy picturesque golf course views. The oversized garage has been extended by approximately 2 feet and houses a Tesla Powerwall battery system. Combined with the solar panel system and assumable home warranty, you'll enjoy energy savings, electric bill credits, and up to 5 days of whole-home backup power during outages. If you've been searching for a home that combines modern updates, energy efficiency, golf course views, and an active lifestyle community, this one truly checks every box. Residents of The Plantation enjoy two championship golf courses, swimming pools, fitness centers, pickleball, tennis, walking trails, clubhouses, endless activities, and a low HOA with no CDD fees. Move-in ready, loaded with upgrades, and designed for worry-free Florida living. Schedule your private showing today before this incredible home is gone!

4704 River Ridge Drive, Leesburg
25233 Lost Oak Circle, Leesburg
$320,000
3 Beds ⋅ 2 Baths ⋅ O6450760 MLS
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 ⋅ G5119346 MLS
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
32656 Oak Park Drive, Leesburg
$249,900
2 Beds ⋅ 2 Baths ⋅ O6451366 MLS
Spectacular Lifestyle, Immaculate Home and Great Neighbors and Community. This is what its all about. Beautifully Updated Home with Solar Panels & Private Wooded and Forest Views in Pennbrooke Fairways Welcome to Pennbrooke Fairways, a sought-after gated 55+ golf community in Leesburg, Florida, where an active lifestyle meets the comfort of home. This beautifully updated 2-bedroom, 2-bathroom single-family home offers an inviting combination of modern improvements, an open and airy feel, and a peaceful natural setting that's becoming harder to find. The moment you walk through the front door, you'll appreciate the wonderful sense of space. Your eyes travel straight through the home to the elegant French doors and the screened lanai beyond, creating an open, light-filled atmosphere that makes the home feel remarkably spacious. Step outside and discover one of this property's most special features: no rear neighbors, just approximately 40 acres of wooded conservation providing a beautiful natural backdrop and a sense of privacy and tranquility. Imagine enjoying your morning coffee or unwinding in the evening surrounded by the sights and sounds of nature! Inside, the home has been refreshed from top to bottom, with new flooring throughout, fresh interior paint, new appliances, and renovated bathrooms with attractive upgrades. The result is a clean, updated interior that feels welcoming from the moment you arrive. Solar panels add an energy-conscious feature, offering buyers another reason to take a closer look. Outside, a lovely combination of new and mature landscaping enhances the home's curb appeal and creates a warm, welcoming first impression. And then there's the Pennbrooke Fairways lifestyle! This gated 55+ community offers a wealth of recreational and social opportunities, including golf, a clubhouse, swimming pool, fitness facilities, tennis, pickleball, and more. Whether you prefer an active calendar filled with activities or simply enjoy the comfort of a welcoming community, there's plenty to appreciate. A beautifully refreshed home, an exceptional wooded backdrop, and a community designed for enjoying the Florida lifestyle — all in one inviting package. Come see why 32656 Oak Park Drive deserves a place at the top of your list!

32656 Oak Park Drive, Leesburg
32919 Indian Woods Drive, Leesburg
$385,000
3 Beds ⋅ 2 Baths ⋅ O6440191 MLS
Virtually Staged. Enjoy the best of Florida living in the established Silver Lake Forest community of Leesburg, where this spacious single-story POOL HOME offers a bright, functional layout, inviting outdoor spaces and a large .29 ACRE LOT! Recent improvements include a NEW POOL PUMP (2024), NEWER ROOF (2023), and SEPTIC DRAIN FIELD (2023), along with an UPDATED A/C & WATER HEATER, plus LUXURY VINYL PLANK & TILE FLOORING throughout. Mature trees, attractive landscaping and a quiet CUL-DE-SAC STREET add to the curb appeal, while a fully FENCED BACKYARD provides plenty of privacy. Inside, high ceilings and abundant natural light enhance the comfortable floor plan, featuring formal living and dining rooms at the front of the home and an open kitchen complete with STAINLESS STEEL APPLIANCES overlooking the family room and casual dining area. The SPLIT BEDROOM LAYOUT offers a private PRIMARY SUITE on one side of the home, complete with a spacious en-suite bath and WALK-IN CLOSET. Two additional bedrooms on the other side of the home share a full guest bath with convenient exterior access to the pool. Step outside to an expansive COVERED LANAI overlooking the PRIVATE SCREENED POOL with a deep end, creating the perfect setting for entertaining, relaxing or enjoying Florida's beautiful weather year-round. Additional highlights include a large laundry room and A/C in the garage for added comfort and flexibility. Silver Lake Forest is a sought-after, established community with a LOW HOA, zoned for “A” RATED Treadway Elementary and conveniently located near US-441, shopping, dining, entertainment and The Villages. Outdoor enthusiasts will appreciate being just minutes from Silver Lake, LAKE HARRIS and the Harris Chain of Lakes. With 3 bedrooms, 2 bathrooms, a generous lot and a fantastic poolside setting, this home checks all the boxes. Assumable VA loan available for qualified buyers – ask for details. Welcome home to Silver Lake Forest and WELCOME HOME!

32919 Indian Woods Drive, Leesburg
24151 Belle Mede Drive, Leesburg
$369,900
3 Beds ⋅ 2 Baths ⋅ G5118829 MLS
This majestic home will serve all your needs. Split bedroom floor plan. The second bedroom has direct entry to a full bath. The 3rd bedroom/den has a murphy bed and custom cabinet that has a drop-down desk and closet. It is so functional. Entertain the entire family with the formal living room, formal dining room, functional kitchen that opens t0 the family room and breakfast area. The laundry room has built in cabinets and a wash sink. Garage is EXTRA DEEP! Great for storing your boat. You will need that boat for fishing on the lakes around here. Some of the best bass fishing around. The Livingroom extends into the 3-season lanai thru glass sliding patio doors. From there you can enjoy sitting on your stone patio. The curb appeal of this home, along with the covered front porch, brick paver driveway, friendly "pineapple exterior light fixtures will impress you, your friends and neighbors. Plantation at Leesburg is a guard gated 55+golf community and rich with exciting amenities. 36 holes of golf, on site restaurant, majestic oak trees and a main club house that makes you think you are at Tara Plantation This home is move in ready, freshly painted interior and professionally cleaned and shined.

24151 Belle Mede Drive, Leesburg
120 Camellia Trail, Leesburg
$109,000
2 Beds ⋅ 2 Baths ⋅ G5119312 MLS
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. Laminate 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 this inviting home has to offer! 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
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