Leesburg Homes with 55+

Leesburg Homes with 55+

Welcome to Leesburg, Florida – a charming city nestled in the heart of Lake County, where sunshine and southern hospitality create the perfect backdrop for your next chapter. Known for its picturesque landscapes and vibrant community, Leesburg is a haven for those seeking a tranquil yet engaging lifestyle. With its rich history, beautiful lakes, and lush parks, this city offers a delightful blend of nature and culture, making it an ideal place to call home.

For those aged 55 and over, Leesburg boasts an array of housing options tailored to meet your needs. The 55+ communities here are designed to enhance your lifestyle, providing not just a home, but a vibrant community filled with like-minded neighbors. These homes often feature modern amenities, low-maintenance designs, and access to recreational facilities that promote an active and fulfilling lifestyle.

Imagine waking up to the serene views of the surrounding lakes, enjoying leisurely strolls through scenic parks, or participating in community events that foster friendships and connections. Leesburg’s 55+ communities offer a variety of activities, from golf and tennis to arts and crafts, ensuring that there’s always something to keep you engaged.

With its convenient location, you’re just a short drive away from the bustling attractions of Orlando, yet far enough to enjoy the peaceful charm of small-town living. Whether you’re looking to downsize or simply embrace a new lifestyle, Leesburg provides the perfect setting for your next adventure. Come discover the welcoming spirit and endless possibilities that await you in this delightful Florida gem!

Newest Leesburg Homes with 55+

25005 Cranes Roost Circle, Leesburg
$289,000
3 Beds ⋅ 2 Baths ⋅ G5118824 MLS
Sunset views on your screened lanai, southern covered front porch for morning coffee, these are just two of the exterior features you will enjoy about this golf course home. 3 Bedrooms, 2 baths, family room, dining room and kitchen dinette enhance your entertaining vibe. Home is move in ready with bathroom updates and kitchen updates. No carpet. just easy-care luxury vinyl. Interior colors reflect the Florida vibrant living. 2 car garage and large laundry room with utility sink round out this perfect home. If you are looking for an easy home to maintain, look no further. The lawn care, landscape trimming and power washing exterior of your home s included , maintained thru the HOA. These snowbird owners have loving taken care and updated this home for you. This neighborhood is special to the Plantation as they have their own private pool to enjoy. You will find friendly, helpful neighbors, driveway parties, pool parties, sports games, dining clubs, within this neighborhood, Home is located on adjacent to a green on the Cranes Roost golf course (currently under renovations) Plantation at Leesburg living will include 3 heated pools 3 club house, one being the Manor that will remind you of Tara Plantation. Pickleball is big, bocce ball, softball, tennis, horseshoes, archery, and many more amenities. RV storage is available. The Oaks bar and grille serves up great food along with music and other entertainment. 36 holes of golf mean you can always get a tee time. Plantation at Leesburg is a 55 plus security gated community within an hour of either coast and the Orlando Parks.

25005 Cranes Roost Circle, Leesburg
6523 Wilander Street, Leesburg
$275,000
3 Beds ⋅ 2 Baths ⋅ G5119002 MLS
Beautiful 3-bedroom, 2-bathroom home located in the desirable 55+ gated community of Highland Lakes. This home’s spacious floor plan offers an eat-in kitchen complete with a sunny breakfast nook surrounded by windows that flood the room with natural light. You will love the impressive amount of cabinet space, bright recessed lighting, and updated countertops, which extend into a stylish countertop breakfast bar. For formal gatherings, a separate dedicated dining room offers the perfect space to entertain family and friends. The spacious primary suite features elegant tray ceilings, two large walk-in closets, and an access door that leads directly from the bedroom into the enclosed patio. The primary bathroom has been updated with a convenient step-in shower and dual-sink vanity. This thoughtful floor plan also includes a large living room with high-set windows that fill the room with light while leaving plenty of wall space. A two-car garage is equipped with a convenient screen door that allows for fresh breezes when working or relaxing in the garage. Other features include updated flooring throughout the home, low-maintenance rock landscaping with stone borders, as well as both an enclosed patio and an exterior patio, offering versatile options for your morning coffee or evening relaxation. The Highland Lakes community is situated in a naturally beautiful setting with miles of scenic nature trails and community fishing lakes, offering an impressive array of amenities that make it easy to stay active, social, and entertained. Residents enjoy indoor and outdoor pools, tennis and pickleball courts, a woodworking shop, a golf driving range, and RV and boat storage. The clubhouse serves as the social hub of the neighborhood, featuring a library, craft room, billiards room, fitness center, meeting spaces, and numerous activity clubs that make it effortless to pursue favorite hobbies or discover new passions. This amazing home is located less than an hour from Orlando International Airport and within a two-hour drive of stunning beaches on both the Atlantic and Gulf coasts. Call today to schedule your private tour and start enjoying the absolute best of Florida living!

6523 Wilander Street, Leesburg
21848 Royal St Georges Lane, Leesburg
$269,900
3 Beds ⋅ 2 Baths ⋅ G5119048 MLS
Virtually Staged. Welcome to this beautifully designed Opal model in the sought-after, resident-owned, gated 55+ community of Royal Highlands! Offering 3 bedrooms, 2 baths, and a spacious, open floor plan, this home combines comfortable living with thoughtful features and valuable updates. Volume ceilings enhance the bright and airy living spaces, while the open great room and dining area provide plenty of room for everyday relaxation and entertaining. The spacious kitchen features beautiful stone countertops, a smoothtop range, closet pantry, and an inviting breakfast nook with a charming bay window that fills the space with natural light. French doors from the main living area lead to the lanai, creating an easy transition between indoor and outdoor living. The generously sized primary suite offers a walk-in closet and an en suite bath with a a walk-in shower. Two additional bedrooms provide flexibility for visiting guests, a home office, or hobby space. Stone countertops throughout the home add a coordinated, attractive finish to the kitchen and bathrooms. Additional conveniences include an inside laundry room and a functional split-bedroom layout. Important updates include a NEW ROOF (2025), WATER HEATER (2022), HVAC SYSTEM (2010), five replacement windows in 2009, five additional replacement windows in 2007, and an updated front entry door (2005). Royal Highlands offers an exceptional active-adult lifestyle with 24-hour staffed gate access and an impressive array of amenities. Residents enjoy indoor and outdoor swimming pools, an 18-hole golf course, driving range, restaurant, pro shop, fitness center, tennis and pickleball courts, bocce ball, shuffleboard, softball, billiards, library, and a recreation center with numerous clubs, activities, and social events. The grand hall hosts concerts, performances, and community gatherings throughout the year. The HOA fee includes cable television and high-speed internet, along with access to RV and boat storage, subject to availability. Conveniently located near shopping, dining, medical facilities, and the Florida Turnpike, Royal Highlands provides easy access to Orlando attractions and area airports. Discover the comfort, convenience, and welcoming lifestyle that make this community such a special place to call home!

21848 Royal St Georges Lane, Leesburg
25345 Green Heron Drive, Leesburg
$250,000
2 Beds ⋅ 2 Baths ⋅ O6449631 MLS
Limited-Time Financing Incentive! Close by November 30th and receive a 2% lender credit through the seller’s preferred lender, subject to lender approval and program terms. Don't miss this opportunity to enjoy a beautifully upgraded, move-in-ready home with potential savings on your closing costs!!!!!! Welcome to this beautifully updated home nestled in a gated community! Enjoy peace of mind and modern style with extensive upgrades throughout. The home features a brand-new roof installed in 2026, along with a fully renovated kitchen showcasing new cabinets, quartz countertops, a new sink, appliances, and updated lighting. New LVP and tile flooring flow throughout the entire home, creating a clean, cohesive look. The bathrooms have also been tastefully updated with new cabinets, quartz countertops, sinks, mirrors, toilets, faucets, and light fixtures. Additional improvements include new baseboards, updated lighting fixtures and ceiling fans throughout, and modern LED recessed lighting for a bright, inviting atmosphere.

25345 Green Heron Drive, Leesburg
32226 Summertree Circle, Leesburg
$249,990
3 Beds ⋅ 2 Baths ⋅ TB8557760 MLS
Completely remodeled from head to toe, this stunning 3-bedroom, 2-bath home in the sought-after 55+ community of Pennbrooke Fairways delivers the fresh, modern feel buyers are looking for! Step inside to discover vaulted ceilings that create an open, airy atmosphere, brand-new luxury vinyl flooring throughout, fresh interior paint, and stylish new lighting and fixtures at every turn. The gorgeous, completely updated kitchen steals the show with crisp shaker cabinets, quartz countertops, a beautiful new backsplash, and brand-new stainless steel appliances. Both bathrooms have been beautifully renovated with retiled showers, new vanities, new toilets, and updated mirrors for a clean, contemporary finish. Outside, enjoy fresh exterior paint and the added peace of mind of a brand-NEW 2026 ROOF AND NEW HVAC. Even the garage has received attention with a refinished floor! But the appeal doesn't stop at the front door! Pennbrooke Fairways offers an incredible lifestyle with affordable HOA fees that include cable TV, high-speed internet, lawn maintenance, and RV and boat storage. Enjoy resort-style amenities including a 27-hole golf course, heated swimming pools and hot tubs, tennis and pickleball courts, an on-site restaurant and salon, gated entry, and plenty of community activities. Beautifully updated, packed with amenities, and ready for its next owner — this is Florida living at its best!

32226 Summertree Circle, Leesburg
6355 Berkshire Pass, Leesburg
$239,900
2 Beds ⋅ 2 Baths ⋅ G5119005 MLS
Welcome to this charming Buckingham model in the sought-after, gated 55+ community of Royal Highlands! Offering 2 bedrooms, 2 baths, and a versatile den/bonus room, this thoughtfully designed home features approximately 1,447 square feet of comfortable living space. Volume ceilings and solid-surface flooring throughout create a bright, open feel with easy maintenance and everyday convenience. The spacious living and dining areas provide a welcoming setting for relaxing or entertaining, while the functional kitchen offers plenty of room for meal preparation and casual dining. The primary suite provides a comfortable retreat, and the additional bedroom and den offer flexibility for visiting guests, a home office, or hobby space. One of the home's highlights is the enclosed lanai, providing additional space to enjoy your morning coffee, unwind with a good book, or simply relax in comfort. Important updates include a NEW ROOF (2025), HVAC system (2016), and water heater (2015), offering valuable information for buyers planning their next chapter. Royal Highlands is a resident-owned, gated 55+ community offering an exceptional array of amenities, including 24-hour staffed gate access, indoor and outdoor swimming pools, an 18-hole golf course with restaurant and pro shop, tennis courts, fitness center, recreation facilities, library, billiards, craft and card rooms, softball field, and a Grand Hall hosting a variety of social activities and events. The monthly HOA fee includes cable and internet, along with access to RV and boat storage. Conveniently located near shopping, dining, medical facilities, and major roadways, Royal Highlands offers the perfect opportunity to enjoy an active Central Florida lifestyle. Come discover all this wonderful community has to offer!

6355 Berkshire Pass, Leesburg
25109 Clifford Hill, Leesburg
$160,000
2 Beds ⋅ 2 Baths ⋅ G5118358 MLS
Virtually Staged. Welcome to 25109 Clifford Hill in Leesburg, Florida! This charming home offers the perfect opportunity to enjoy the Florida lifestyle with a spacious, inviting layout and plenty of natural light throughout. Step inside to find updated vinyl flooring, comfortable living spaces, and a functional kitchen featuring an abundance of cabinetry, providing plenty of storage for all your kitchen essentials. The home also offers additional built-in cabinetry and storage throughout, making it easy to stay organized. Both bedrooms provide comfortable spaces to relax and unwind, while the bathrooms offer convenience and functionality. Major updates include a metal roof installed in 2021 and an A/C system replaced in 2020! Outside, you'll love the covered front porch, the perfect spot to enjoy your morning coffee, relax with a good book, or simply soak up the beautiful Florida weather. The nicely maintained landscaping adds to the home's curb appeal, while the surrounding outdoor space provides room to enjoy the sunshine. Whether you're looking for a year-round residence or a seasonal Florida retreat, this home has so much to offer and is ready for your personal touch! Conveniently located near shopping, restaurants, medical facilities, and everything Leesburg has to offer. Don't miss your opportunity to make this home your own. Schedule your private showing today!

25109 Clifford Hill, Leesburg
5124 Links Lane, Leesburg
$400,000
3 Beds ⋅ 2 Baths ⋅ G5118654 MLS
Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed! Seller's preferred lender is willing to contribute 1% of the loan amount toward the buyer's interest rate buy-down. GOLF COURSE LIVING AT ITS FINEST! Welcome to 5124 Links Lane, where beautiful fairway views, resort-style amenities, and the Florida lifestyle you've been dreaming of come together in the highly desirable, guard-gated Royal Highlands 55+ community! Perfectly positioned on an oversized homesite overlooking the 12th fairway of Monarch Golf Course, this beautifully maintained Windsor model offers the ideal combination of comfort, privacy, and effortless entertaining. Imagine starting your mornings with coffee on your spacious lanai, watching golfers make their way down the fairway, and ending your evenings surrounded by peaceful golf course scenery. This is more than a home. It's a lifestyle! From the moment you arrive, you'll appreciate the attractive curb appeal, lush landscaping, generous setback from the street, and extra-long driveway with plenty of room for visiting friends and family. Inside, the thoughtfully designed 3-bedroom, 2-bath split floor plan offers spacious living areas, comfortable guest accommodations, and the flexibility to create a home office, hobby room, or personal retreat. The inviting kitchen features stainless steel appliances less than five years old and a stylish farmhouse sink. Laminate flooring throughout the family room and bedrooms adds warmth and easy maintenance, while plantation shutters and dual-pane windows provide timeless appeal. Even better, many of the big-ticket updates have already been taken care of! Enjoy peace of mind with a 2020 ROOF, 2018 HVAC, beautifully updated primary bathroom with frameless-style heavy glass shower enclosure (2025), plantation shutters (2025), refreshed landscaping (2023), and new garage door opener (2025). But what truly makes this property special is the lifestyle waiting just beyond your front door! Royal Highlands feels like your own private resort, offering an exceptional collection of amenities designed to keep you as active or relaxed as you choose. Spend your mornings on the beautiful 18-hole Monarch Golf Course, enjoy a refreshing swim in the indoor or outdoor pools, challenge friends to pickleball or tennis, stay active in the fitness center, or gather with neighbors for social events at the impressive recreation center and grand hall. With on-site dining, recreational activities, and opportunities to make lasting friendships, every day can feel like a vacation! And when you're ready to explore, you'll love the convenient access to shopping, restaurants, grocery stores, Clermont, the Florida Turnpike, and everything Central Florida has to offer. Orlando International Airport and the world-famous Disney attractions are approximately 50 minutes away, making travel and visits from family a breeze. Why settle for an ordinary retirement when you can enjoy an extraordinary lifestyle? Whether you're looking for your full-time Florida retreat or the perfect seasonal escape, this golf course home delivers the space, scenery, amenities, and community you've been searching for. Your next chapter deserves a beautiful backdrop. Schedule your private showing today and discover why life is better on the fairway at Royal Highlands!

5124 Links Lane, Leesburg
27239 White Plains Way, Leesburg
$305,000
2 Beds ⋅ 3 Baths ⋅ G5118636 MLS
Virtually Staged. QUICK CLOSING & MOVE-IN POSSIBLE! Short 250 Feet walk to the amenities, golf course, restaurant & pub, Embrace the exterior maintenance-Free Lifestyle in this 2 bedroom, 2 1/2 bath with low maintenance concrete block & stucco home with 2 car garage and inside laundry room. Enjoy the luxury feel of wood cabinetry and open kitchen perfect for entertaining, 3 seat bar-top, stainless kitchen appliances that stay, indoor laundry room with washer & dryer that stay, Low HOA of $303/month includes full lawn care, irrigation water & system, new roof when needed, exterior painting, high-speed internet, Wi-Fi, and over 200 cable channels. Community has On-site RV and boat parking available, . Safe & Secure gated community With no yardwork nor exterior maintenance to worry about, What will you do with all your free time? Arlington Ridge is more than a community it’s a way of living. Spend your mornings on the championship 18-hole golf course (no Membership Required. Pay only when you play as well as numerous amenities at no extra charge, Spend your afternoons at the heated pools or well-equipped fitness center with a pool view..., and your evenings with friends and neighbors at the on-site restaurant, tavern, or free movie theater. Enjoy tennis, pickleball, bocce, billiards, all just a 1 block walk or quick golf cart ride away. Take a peaceful stroll, walk the dog or bike ride along sidewalk lined streets. THIS IS A GOLF-CART FRIENDLY COMMUNITY WITH MULTIPLE CARD , HOBBY AND GAMES GROUPS. Conveniently located near shopping, dining, medical services, and a short drive to Orlando’s attractions and both coasts’ beaches, this home blends resort-style living with everyday practicality. One of the most affordable communities to purchase homeowner's insurance in. YOU DO NOT HAVE TO PURCHASE A SOCIAL NOR GOLF MEMEBRSHIP TO PURCHASE IN COMMUNITY OR TO USE AMENITIES.

27239 White Plains Way, Leesburg
4634 Belle Grove, Leesburg
$237,000
2 Beds ⋅ 2 Baths ⋅ G5118972 MLS
PEACEFUL POND & CONSERVATION VIEWS + RESORT-STYLE 55+ LIVING! Welcome to 4634 Belle Grove, tucked away on a quiet cul-de-sac in the highly desirable Plantation at Leesburg. This spacious 2-bedroom, 2-bath home offers approximately 1,692 square feet of comfortable living space with a layout designed for both everyday living and entertaining. Inside, you'll find generous living and dining areas, an eat-in kitchen with abundant cabinetry and counter space, and a bright Florida room where you can relax and enjoy the peaceful setting. The primary suite offers a private bath with dual sinks and an oversized shower, while the second bedroom provides plenty of space for guests, an office, or hobbies. Additional highlights include wood flooring, double-pane windows, inside laundry, a 2-car carport, golf cart garage, and a long driveway offering ample parking. Step outside to one of the home's best features—a tranquil rear setting overlooking the pond and conservation area. Enjoy your morning coffee, unwind in the evening, or simply take in the Florida scenery from your own backyard. Located in The Plantation at Leesburg, residents enjoy an active 55+ lifestyle with an incredible selection of amenities, including gated entry, multiple clubhouses and activity centers, three community pools, fitness facilities, pickleball, tennis, bocce, softball, archery, woodworking facilities, walking areas, and an extensive calendar of clubs, social events, and activities. Golf enthusiasts will love having two 18-hole golf courses right within the community, and golf-cart-friendly streets make it easy to get around and enjoy everything The Plantation has to offer. With a newer HVAC system (2023) and roof (2025), peaceful water and conservation views, and access to one of Leesburg's most amenity-rich active-adult communities, this home offers the Florida lifestyle you've been looking for. Schedule your private showing and come see what makes 4634 Belle Grove such a special place to call home!

4634 Belle Grove, Leesburg
32543 Oak Park Drive, Leesburg
$239,247
2 Beds ⋅ 2 Baths ⋅ G5118618 MLS
Enjoy beautiful golf course views from this two-bedroom, two-bath home in Leesburg’s Pennbrooke Fairways 55+ community! The fully enclosed, air-conditioned lanai offers a comfortable place to relax, entertain, or simply take in the peaceful greens beyond. An inside laundry room provides versatile space for an office, craft room, or your favorite hobbies, adding everyday convenience and flexibility. With its inviting golf course setting and comfortable indoor spaces, 32543 Oak Park Drive is a wonderful place to make yourself at home.

32543 Oak Park Drive, Leesburg
647 Timbercrest Drive, Leesburg
$216,247
2 Beds ⋅ 2 Baths ⋅ G5118789 MLS
Enjoy comfortable Florida living at 647 Timbercrest Drive in Pennbrooke Fairways, a 55+ community in Leesburg. This furnished two-bedroom, two-bath home features an open layout with laminate flooring and no carpet in the main living areas. The kitchen opens to the main living space and offers newer appliances, an island with the range, and a breakfast bar that keeps the cook connected to family and guests. Outdoor living is a highlight, with a spacious screened birdcage and a covered lanai area—ideal for morning coffee, outdoor dining, or relaxing in the shade. Additional green space behind the home provides a welcome sense of openness and more breathing room between you and the neighbors to the rear. A 2022 reroof adds to the appeal of this inviting, furnished home.

647 Timbercrest Drive, Leesburg
Start Your Search