Leesburg Homes with 55+

Leesburg Homes with 55+

Welcome to Leesburg, Florida—a charming gem nestled in the heart of Lake County. Known for its friendly atmosphere and vibrant community, Leesburg offers a perfect blend of small-town charm and modern amenities, making it an ideal destination for those seeking a peaceful yet engaging lifestyle.

One of the standout features of Leesburg is its welcoming environment for active adults, particularly those aged 55 and over. The city is home to numerous 55+ communities that provide a wealth of opportunities for socializing, recreation, and relaxation. These neighborhoods are thoughtfully designed to cater to the needs of retirees and active adults, featuring amenities such as clubhouses, fitness centers, swimming pools, and organized activities that foster a strong sense of community.

In addition to its inviting communities, Leesburg boasts stunning natural beauty with its picturesque lakes and lush parks. Residents can enjoy leisurely strolls along the waterfront, fishing, or picnicking in the many green spaces that dot the area. The city's rich history is also on display, with charming downtown shops, local eateries, and cultural events that celebrate the vibrant spirit of the region.

With its affordable housing options, friendly neighborhoods, and a plethora of recreational activities, Leesburg is not just a place to live; it’s a place to thrive. Whether you’re looking to settle down in a cozy single-family home or a maintenance-free villa, the 55+ communities in Leesburg are designed to enhance your lifestyle and provide you with the perfect backdrop for your next chapter. Come discover the warmth and charm of Leesburg, where your dream home awaits!

Newest Leesburg Homes with 55+

$129,900
2 Beds ⋅ 2 Baths ⋅ G5118443 MLS
Welcome to easy Florida living in this beautifully maintained 2-bedroom, 2-bath home offering 1,236 square feet of comfortable living space. Bright, inviting, and filled with natural light, this home has been thoughtfully cared for and is ready for its next owner. The spacious living room is highlighted by impressive panoramic windows that create an open, airy feel and provide plenty of natural light. Fresh interior finishes, attractive ceiling fans, updated light fixtures, and beach-inspired touches give the home a relaxed Florida style. One of the standout features is the enclosed Florida room with glass windows and heat, providing additional year-round space for relaxing, entertaining, hobbies, or enjoying your morning coffee. The well-maintained kitchen offers a functional layout with plenty of room for everyday meal preparation. Both bedrooms are comfortably sized, with the primary suite featuring a private bath with walk-in shower. The guest bathroom includes a tub, offering added convenience for visitors. A large laundry room provides valuable additional storage space. Outside, the long driveway, vinyl siding, and refreshed exterior add to the home’s curb appeal. Additional improvements include newer windows, a well-maintained roof-over, and a 2022 HVAC system. Whether you are searching for a full-time Florida residence or a seasonal getaway, this home offers comfort, functionality, and plenty of space to enjoy. Located in Hawthorne at Leesburg, a gated, resident-owned 55+ cooperative waterfront community, residents enjoy an impressive selection of amenities and activities. The $397 monthly maintenance fee includes water, sewer, lawn mowing, private emergency services, and secure storage for RVs, boats, and trailers. The community clubhouse features seating for approximately 550, a full-time program coordinator, and more than 100 activities, along with a hospitality lounge, card rooms, craft and fine arts rooms, billiards, fitness center, and library. Residents can also enjoy an outdoor geothermal-heated pool, two enclosed therapeutic pools, excellent fishing, beautifully landscaped grounds, lakes with illuminated fountains, and a relaxing gazebo. Hawthorne’s private, marina offers 120 boat slips with direct access to the Harris Chain of Lakes and beyond.

408 Palo Verde Drive, Leesburg
$309,900
3 Beds ⋅ 2 Baths ⋅ G5118394 MLS
Virtually Staged. Tucked on a cul-de-sac in the gated 55+ community of Royal Highlands, this expanded Balmoral offers a peaceful conservation setting with no rear neighbors. The 3-bedroom, 2-bath home has 1,559 square feet of living space and solid surface flooring throughout, including engineered hardwood and ceramic tile. The eat-in kitchen features a breakfast bar, closet pantry, built-in microwave and recessed lighting. It opens to a spacious great room with sliding doors to the screened lanai, where vinyl stacking windows and a convenience bar with a refrigerator make the space easy to enjoy in every season. An adjoining patio offers another spot to relax outdoors and take in the natural setting. The primary suite includes a walk-in closet, jetted tub, separate shower and dual-sink vanity. An inside laundry room leads to the two-car garage, while plantation shutters and a screened front entry add to the home’s appeal. All appliances, the water heater and the HVAC system have been replaced within the last five years. Royal Highlands offers indoor and outdoor pools, pickleball and a convenient Leesburg location near the Florida Turnpike.

4512 Inverness Drive, Leesburg
$499,900
3 Beds ⋅ 4 Baths ⋅ G5118361 MLS
Virtually Staged. Welcome to this truly one-of-a-kind custom home, privately positioned at the end of a quiet cul-de-sac in the gated 55+ community of Legacy of Leesburg. Offering an impressive 3,362 square feet of living space, this spacious residence features three bedrooms, three-and-a-half bathrooms and an oversized lot backing to a peaceful conservation area. Beautiful curb appeal begins with mature landscaping, Colorado flagstone accents and an attractive water feature. Inside, the thoughtfully designed floor plan places the primary living areas on the first floor and provides generous space for both comfortable everyday living and entertaining. The kitchen features 42-inch oak cabinetry with crown molding, pull-out drawers, stainless-steel appliances, granite countertops, a center island and abundant storage. The oversized primary suite is a relaxing retreat with two walk-in closets, dual raised vanities, a garden tub and a remarkable wraparound walk-through shower with dual showerheads. An additional Florida room with dedicated air conditioning offers the perfect setting to unwind while enjoying the natural surroundings and visiting wildlife. Residents of Legacy of Leesburg enjoy a resort-style heated pool, clubhouse, fitness center, pickleball, tennis, bocce, softball, walking and biking trails, and a private riverfront nature park. This exceptional home offers space, privacy and an active Florida lifestyle—schedule your private showing today!

5353 Treasure View Way, Leesburg
$124,247
2 Beds ⋅ 2 Baths ⋅ G5118283 MLS
Welcome to 32322 Oak Park Drive in Pennbrooke Fairways, a Housing for Older Persons 55+ community in Leesburg. This 2-bedroom, 2-bath manufactured home is situated on a private wooded preserve lot, offering a peaceful setting and added privacy with no homes directly behind you. Inside, you'll find all-new flooring throughout with NO CARPET, plus a beautifully upgraded kitchen featuring new cabinets, countertops and stainless steel appliances. Both the primary and guest bathrooms have also been updated, giving the home a fresh, move-in-ready feel. A BONUS ROOM provides additional flexible living space-perfect for a home office, hobby room, den or additional sitting area. You'll also appreciate the convenience of INDOOR LAUNDRY. The ROOF was replaced in 2017, and to make this home even more appealing, the FURNITURE AND GOLF CART CONVEY WITH THE HOME! With its updated interior, comfortable floor plan, private wooded preserve setting and included furnishings and golf cart, this home is ready for you to start enjoying the Florida lifestyle.

32322 Oak Park Drive, Leesburg
$525,000
3 Beds ⋅ 3 Baths ⋅ O6445328 MLS
Picture your mornings starting on your own private, second-story balcony, sipping coffee as the sun rises over the quiet woods behind your home. Located in one of Leesburg’s premier communities, this beautiful property welcomes you with a picture-perfect paver driveway, a cozy front porch, and the effortless upkeep of premium Rhino Shield exterior paint. Inside, warm, real hardwood floors flow through an open and airy layout. Step into a light-filled gourmet kitchen where baking and hosting feel effortless. Crisp double ovens stand ready for holiday meals, while a generous central island and breakfast bar invite friends to pull up a stool and chat while you cook. This beautiful space flows naturally into a formal dining room, making it easy to transition from casual meal prep to elegant candlelit dinners. Downstairs also features a cozy fireplace in the living room and a bright, dedicated office that could easily become a fourth bedroom or a creative studio. The layout offers a rare and luxurious setup with two separate primary suites. The main-floor suite is perfect for guests, while the upstairs serves as your ultimate personal sanctuary, complete with a charming reading loft. When it's time to unwind, step out into the massive, screened-in lanai. With a dramatic two story screen and a backyard that backs right up to the trees with no rear neighbors, it feels like your own private, peaceful oasis. Welcome home.

5384 Aurora Drive, Leesburg
$204,900
2 Beds ⋅ 2 Baths ⋅ G5117682 MLS
RENOVATED and ready for immediate occupancy! This single-family Villa with courtyard entrance is PRICED TO MOVE - Don't wait! Furniture negotiable | 2-bedroom split lay out with 2 full bathrooms | NEW HVAC (August 2026) | OVER-SIZED garage features 274sf with screened entry | NEW stainless appliances | washer and dryer included | GRANITE countertops in kitchen | PORCELAINE PLANK TILE FLOORING throughout and nearly new carpet and pad in bedrooms | NEW BLINDS |NEW FRONT DOOR and hardware | Fresh interior paint | Covered enclosed rear patio has NEW PERGO luxury vinyl plank flooring AND NEW vinyl WINDOWS scheduled for install, making this currently screen enclosed space ideal for year-round enjoyment. | Skylight and solar tube add loads of natural lighting | Dining and living room combination with vaulted ceiling, 8-foot sliding glass door to access the covered lanai. The Primary Retreat features makeup vanity with single sink, walk-in closet, shower-tub combination and skylight. This split bedroom floorplan boasts the Guest Bedroom at the front of the home, over-looking the courtyard, features dual closets and direct access to the guest bath; featuring updated vanity and shower-tub combination. Entire interior freshly painted April 2025 | Roof 2024 | HVAC 2026 | Water Heater approximately 6 years new | Updated electric panel | 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!

26032 Newcombe Circle, Leesburg
$357,000
2 Beds ⋅ 2 Baths ⋅ G5118174 MLS
Virtually Staged. REFINED FLORIDA LIVING in The Plantation at Leesburg! Beautifully updated and situated on a landscaped CORNER LOT in desirable Nottoway Village, this 2BR/2BA + STUDY home offers 2,051 sq ft, an ENCLOSED FLORIDA ROOM and expansive SCREENED LANAI. With extensive recent improvements, this home shows beautifully with a LIKE-NEW, MOVE-IN READY feel! The interior features CROWN MOLDING, and a neutral color palette ready to complement any décor. NEW 2026 LUXURY VINYL PLANK flooring throughout the main living areas and bedrooms. The UPDATED KITCHEN shines with NEW QUARTZ countertops, freshly painted cabinetry with SOFT-CLOSE doors/drawers and new hardware, NEW Samsung stainless RANGE, DISHWASHER AND REFRIGERATOR, NEW SINK and FAUCET, center ISLAND, pantry, and abundant storage. A SEPARATE DINING ROOM just off the kitchen provides the perfect setting for easy entertaining. The spacious PRIMARY SUITE features a CUSTOM WALK-IN CLOSET and private ensuite with dual vanities, makeup area, garden tub and separate shower. The GUEST BEDROOM and adjoining STUDY share a convenient JACK-AND-JILL BATH, creating flexible space for guests, a home office or additional living needs. Relax in the nearly 27-ft ENCLOSED FLORIDA ROOM, then step outside to the LARGE SCREENED CAGE—an inviting place to enjoy Florida evenings and gaze at the stars. Major improvements include NEW AC 2026, NEW WATER HEATER 2026 and NEW ROOF 2024, plus IMPACT WINDOWS in select areas, freshly painted interior, solar board attic barrier and foam insulation in the cinder blocks. The EXTENDED 2-CAR GARAGE features an epoxy floor, cabinetry and WORKBENCH. Enjoy the sought-after 55+ GOLF COMMUNITY lifestyle with pools, fitness, pickleball, tennis, golf, clubhouses, restaurant and activities. BEAUTIFULLY UPDATED, LIKE-NEW & MOVE-IN READY—schedule your private showing today!

24445 Madewood Avenue, Leesburg
$525,000
4 Beds ⋅ 4 Baths ⋅ G5118222 MLS
LAKEFRONT. POOL. PRIVACY. AND A TRUE CUSTOM HOME. Tucked away on a quiet cul-de-sac in the desirable 55+ community of Royal Highlands, this impressive 3,318 sq. ft. custom home offers 4 bedrooms, 4 baths, a home office/bonus room, an oversized 3-bay garage and beautiful views of Lake Monarch. Major improvements include a NEW ROOF in 2025, TWO HVAC SYSTEMS replaced in 2020 & 2022, 8 NEW WINDOWS in 2026 plus 2 additional windows replaced in 2024. A transferable termite bond provides additional peace of mind. From the moment you enter, the spacious, open design draws your eye through the great room to the pool and sparkling lake beyond. Multiple pocket sliding doors open the living space to the screened pool and lanai, creating an exceptional setting for entertaining or simply enjoying peaceful Florida mornings and gorgeous sunrises over the water. The expansive great room features a gas fireplace surrounded by custom built-in display shelving. The bright, open kitchen offers newer appliances, abundant cabinetry and counter space, an extended breakfast bar and an enormous walk-in pantry. Just off the kitchen, a second large screened porch creates another inviting outdoor living and dining space overlooking the private backyard setting with mature oaks. The primary suite is truly unique, featuring generous closet space and separate his-and-hers bathrooms connected by a shared walk-through shower. Two guest bedrooms share a convenient Jack-and-Jill bath, while an additional guest bedroom provides flexibility for family and visitors. The light-filled office/bonus room enjoys beautiful views and could easily serve as a craft or hobby room. Even the oversized laundry room was designed with functionality in mind, offering extensive cabinetry, counter space and a utility sink. And then there’s the garage! The oversized 3-bay configuration includes dedicated golf cart space, an enclosed workshop and a rear roll-up door providing convenient access for lawn equipment and projects. Royal Highlands offers an active Florida lifestyle with indoor and outdoor pools, pickleball, tennis, softball, fitness and recreation facilities, clubs, entertainment, billiards, library and more. The community is also home to the Monarch Golf Club and its restaurant. With substantial recent improvements, exceptional indoor and outdoor living spaces, a private pool and a premium Lake Monarch setting, this is anything but the typical Florida home.

5409 Essex Court, Leesburg
$229,900
2 Beds ⋅ 2 Baths ⋅ G5118163 MLS
Virtually Staged. BEAUTIFULLY RENOVATED VILLA OFFERING EASY, LOCK-AND-LEAVE FLORIDA LIVING! Whether you're searching for a full-time residence or a seasonal getaway, this thoughtfully updated villa offers the perfect combination of comfort, convenience, and low-maintenance living. With more than $50,000 in improvements, much of the work has already been done for you! Step inside to discover a bright, inviting interior featuring updated flooring throughout, fresh paint, modern lighting, and a beautifully remodeled kitchen. Four skylights fill the home with natural light, while a natural gas fireplace adds warmth and character to the living area. One of the home's standout features is the enclosed lanai, thoughtfully incorporated into the living space to create additional room for entertaining, a home office, or a comfortable retreat for visiting guests. The updated primary bathroom features a raised vanity, and the home's extensive improvements continue with a new roof and skylights (2022/2023), HVAC system, electrical panel (2024), garage door (2024), and water heater (2025). Even the garage has received attention with recessed lighting, providing flexibility for additional seasonal use. Step outside to enjoy your own private courtyard, an inviting space for morning coffee or relaxing Florida evenings. LOVE TO TRAVEL? THIS IS THE LOCK-AND-LEAVE LIFESTYLE YOU'VE BEEN LOOKING FOR! The HOA takes care of many exterior maintenance responsibilities, including irrigation and termite protection, includes a roof replacement reserve, AND OFFERS FREE BOAT AND RV STORAGE—an added convenience that's perfect for enjoying the Florida lifestyle. Spend less time worrying about home maintenance and more time enjoying everything Central Florida has to offer. With extensive renovations, flexible living spaces, and the convenience of villa living, this home is ready for your next chapter. Pack your bags and start enjoying the Florida lifestyle!

5440 Rosewall Circle, Leesburg
$299,900
2 Beds ⋅ 2 Baths ⋅ G5118162 MLS
Welcome to your new home in The Plantation at Leesburg! With 2 golf courses, pools, tennis, restaurant, gated access and plenty of community events, the Planation is the perfect active adult community! Pulling up to your new home you will notice the beautiful corner lot off of a shady, oak lined street. Walking in, you will be greeted by the open Great Room (16x25 approximately) and two sets of sliding glass doors leading out to your screened pool oasis. A nicely updated kitchen with Granite and Tiled Backsplash sits off to the West side of the home along with garage access. To the East side of the home are the primary bedroom (with access to the pool), a second bedroom and an office that could be a third bedroom. Bonuses include a pool heater / solar heating, garage door retractable screen, newer water heater, roof and ac. The home is situated just an hour North of Orlando, 15 minutes from the newest Villages development, and moments to Clermont / Minneola. Come take a look today!

3916 Manor Oaks Court, Leesburg
$69,900
2 Beds ⋅ 2 Baths ⋅ G5118125 MLS ⋅ Chesterbrook Two BLDG.
Why rent when you can own? This updated 2-bedroom, 2-bathroom condo gives you the opportunity to put your money toward something you own instead of paying rent. This home comes furnished. Please contact the agent for details. The current owner has made several major improvements over the past few years, so much of the work has already been done. The central heat and air system is only about 3 months old. The refrigerator, stove/oven, range hood, dishwasher, and stackable washer and dryer are also about 3 months old. The electrical panel was upgraded and inspected about 2 months ago, and the kitchen backsplash and farmhouse sink were added about 5 months ago. Laminate flooring was installed approximately 3 years ago, and the entire home, including the Florida Room, was painted around the same time. Outside, you’ll have a private backyard area, and the Florida Room gives you additional space to relax or entertain. The community also offers amenities including a clubhouse and swimming pool. If you’ve been comparing the cost of renting with owning, this one is worth a look. Call today to schedule a showing!

500 Newell Hill Road Unit 105B, Leesburg
$395,000
3 Beds ⋅ 2 Baths ⋅ O6443840 MLS
Virtually Staged. Some mornings are meant to start slowly, coffee in hand, the sliding doors open, and a quiet Central Florida sunrise over the trees. That's the rhythm waiting at 26939 Honeymoon Ave, a beautifully reimagined 3-bedroom, 2-bath home in the gated community of Legacy of Leesburg. Step inside and you'll feel it right away: this one has been completely remodeled, top to bottom. A brand-new kitchen anchors the heart of the home, both bathrooms have been fully renovated, and fresh flooring flows seamlessly through all 2,002 square feet. New appliances, new fixtures, and fresh paint mean there's truly nothing left to do but move in and unpack. The real magic happens out back. The extended, screened lanai is built for the way you actually want to live: long dinners with friends, a good book on a breezy afternoon, and evenings unwinding in your own private hot tub. It's the kind of space that turns an ordinary Tuesday into something that feels like vacation. And beyond your door, Legacy of Leesburg delivers a lifestyle to match. Wander 275 acres of nature preserve and trails along the Palatlakaha River, then trade the quiet for the buzz of the clubhouse: resort-style pool and spa, fitness center, pickleball, tennis, bocce, and dozens of clubs led by a full-time activities director. Lawn care and cable are included, so your weekends stay yours. Boat and RV storage are on-site, and Orlando's airport and attractions sit less than an hour away. Homes this thoroughly updated, in a setting this special, don't stay quiet for long. Come see what living at Legacy really feels like, then start planning that first morning on the lanai.

26939 Honeymoon Avenue, Leesburg
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