Leesburg Homes with Pool Community Features

Leesburg Homes with Pool Community Features

Welcome to Leesburg, Florida, a charming city nestled in the heart of Lake County. Known for its picturesque lakes, vibrant community spirit, and rich history, Leesburg offers a delightful blend of small-town charm and modern amenities. With its warm climate, residents enjoy year-round outdoor activities, making it an ideal place for those who love nature and adventure.

One of the standout features of Leesburg is its array of homes with pool community options. Imagine coming home to your own private oasis, where you can unwind and cool off in your backyard pool. These communities are designed for both relaxation and social engagement, fostering a sense of belonging among neighbors. Whether you’re hosting summer barbecues or enjoying a quiet evening under the stars, having a pool at your doorstep transforms your living experience into a luxurious retreat.

In addition to the stunning homes, Leesburg boasts a variety of amenities, including parks, shopping centers, and local dining options that cater to every palate. The city’s commitment to community events and recreational activities ensures that there’s always something happening, from farmers' markets to seasonal festivals.

For families, the area is served by reputable schools and offers a safe, welcoming environment for children to grow and thrive. With its friendly atmosphere and beautiful surroundings, Leesburg, Florida, is more than just a place to live; it’s a place to call home. Explore the homes with pool community options in Leesburg and discover the perfect blend of comfort, convenience, and community. Your dream home awaits!

Newest Leesburg Homes with Pool Community Features

$69,900
2 Beds ⋅ 2 Baths ⋅ Leesburg Chesterbrook 02 Condo Ph 01 SubDv. ⋅ 34748 Zip Code
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. 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 ⋅ Legacy Leesburg SubDv. ⋅ 34748 Zip Code
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
$180,000
2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Belle Grove SubDv. ⋅ 34748 Zip Code
Prepare to be WOWED by this beautifully maintained home featuring TWO OWNER’S SUITES, each offering comfort and privacy, along with 2 full bathrooms! This move-in-ready home has been lovingly cared for and offers numerous valuable upgrades, including a newer electrical panel inside and out, A/C (2016), newer hot water heater, storm doors, gutters (2019), updated ductwork underneath the home, added surge protection, and a desirable GOLF CART GARAGE. This is truly a MUST-SEE home and is ready for a QUICK SETTLEMENT! Located in the gated Plantation at Leesburg, you’ll enjoy an active 55+ lifestyle with an incredible variety of amenities, including 2 golf courses, 3 swimming pools, walking trails, pickleball, tennis, horseshoes, and so much more. Hop in your golf cart and head over to The Oaks Restaurant for a cold drink, great food, and entertainment—all without leaving the community! Come see everything this wonderful home and community have to offer!

25524 Belle Helene, Leesburg
$300,000
3 Beds ⋅ 2 Baths ⋅ Plantation/Leesburg Manor View V SubDv. ⋅ 34748 Zip Code
Welcome to 24817 Riverboat Bend, located in the desirable Plantation at Leesburg, a gated 55+ golf cart community with full-time security offering an active Florida lifestyle! This inviting 3-bedroom, 2-bath home features a comfortable, open layout with plenty of natural light, a 2-car garage, and space for everyday living and entertaining. A NEW ROOF was installed in 2024, and the primary bathroom has been updated with a walk-in shower featuring safety grab bars for added convenience and accessibility. Plantation at Leesburg offers an impressive selection of amenities, including two 18-hole golf courses, activity centers, clubhouses, heated swimming pools, fitness centers, tennis, pickleball, walking and biking opportunities, on-site dining, and numerous clubs and activities. Enjoy the convenience of traveling throughout this golf cart-friendly community while taking advantage of the resources Plantation at Leesburg provides. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers a wonderful combination of comfort, convenience, security, and an active lifestyle. Schedule your private showing today!

24817 Riverboat Bend, Leesburg
$340,000
2 Beds ⋅ 2 Baths ⋅ Legacy/Leesburg Un 6 Ph Vii SubDv. ⋅ 34748 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bathroom, plus office, home with a water view, in the highly desirable Legacy of Leesburg 55+ gated community. This residence offers a bright, open layout, peaceful water views, and a long list of thoughtful upgrades designed for comfort, convenience, and low-maintenance living. The living room features vinyl plank flooring and opens seamlessly to the kitchen, dining area, and enclosed lanai. The kitchen includes quartz countertops, a cast porcelain sink, wood cabinetry, garbage disposal faucets, and stainless-steel appliances including an electric stovetop, microwave, built-in oven, and refrigerator. A charming breakfast area with a chandelier overlooks the water, creating a serene place to enjoy morning coffee. The enclosed lanai features tinted hurricane-grade windows, with the original sliding doors stored in the garage, and the screened patio includes a SunSetter roll-out shade for comfortable outdoor living. The primary bedroom offers carpeted flooring and a tranquil water view. Its en-suite bathroom includes ceramic tile, dual sinks with granite countertops, wood cabinetry, a walk-in shower, and a spacious walk-through closet. The second bedroom features carpet, a ceiling fan with light, and a full closet, while the second bathroom includes granite countertops, wood cabinetry, ceramic tile flooring and a tub-shower combination. The den/office provides a quiet, flexible space bonus room with carpet and a ceiling fan. The home includes a two-car garage with a coated floor, tankless water heater, wash bin, pull-down attic access, and a garage screen for airflow. A pavered driveway, exterior landscaping, and a sprinkler system add to the home’s curb appeal. The property is conveniently located near the community’s back entry and exit for easy access. This homes low-maintenance lifestyle, includes lawn mowing, blowing, edging, cable, and internet in the HOA fee. Legacy of Leesburg offers an exceptional array of amenities included in the monthly association fees. Clock Tower Hall serves as the community’s central social hub, hosting daily events, performances, bingo, dances, group exercise classes, and more, supported by two catering kitchens for gatherings. Indoor recreation includes a state-of-the-art fitness center, an aerobics studio, a card room, craft room, billiards, ping-pong tables, and a library and media center with computers available for residents. Outdoor amenities feature a resort-style heated pool and spa with walk-in beach entry, lap swim area, water aerobics depth, cabana, and outdoor bar. Sports facilities include a softball field, tennis courts, pickleball courts, bocce courts, horseshoe pits, and shuffleboard. The community is surrounded by 275 acres of conservation areas with 19 ponds and 13 nature trails perfect for walking, biking, fishing, and wildlife viewing. For RV and boat owners, Legacy of Leesburg provides a dedicated River Park RV lot and a secure storage area. All amenities are available to residents at no additional cost beyond the monthly fees, creating a lifestyle centered around nature, recreation, and active adult engagement.

5811 Greenbriar Loop, Leesburg
$192,900
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands Condo Ph K SubDv. ⋅ 34788 Zip Code
Great home in the centrally located community of Scottish Highlands. This 2 bedroom, 2 bath home would be ideal for your retirement. The home has a living room, dining room combo as well as a large separate great room. It is landscaped with mature landscaping and irrigation system. The roof was replaced in 2025. The community has an outdoor pool as well as an indoor pool. Other features include clubhouse, tennis, pickleball, and bocci couts. There is onsite parking for RV’s and boats. The home is well located for a short walk to the amenities.

1113 Ben Hope Drive, Leesburg
$250,000
2 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph Ie Sub SubDv. ⋅ 34748 Zip Code
Welcome to 642 Glen Oaks Drive, located in Pennbrooke Fairways, a gated and guarded 55+ community just five minutes south of The Villages! This bright and spacious 2-bedroom, 2-bath home features an open living area and a versatile bonus space filled with natural light. The kitchen and bathrooms showcase newly installed countertops complemented by modern black fixtures, while three new ceiling fans add comfort and style throughout. The generously sized primary suite offers a large walk-in closet and private bath. The guest bedroom connects directly to the second bathroom, allowing it to function as a private ensuite while remaining accessible to visitors. Additional highlights include a water-softener system and a peaceful backyard with no rear neighbors. Pennbrooke Fairways offers three golf courses, including two executive nine-hole courses and one regulation nine-hole course, along with resident golf packages. Community amenities include swimming pools, recreation centers, a restaurant, hair salon, library, RV and boat storage, dump and wash stations, and 24-hour gated security. HOA services include cable, internet, and lawn cutting. With Orlando less than an hour away and Tampa and Daytona Beach within approximately 90 minutes, this location provides convenient access to shopping, entertainment, and easy day trips. Schedule your private showing today!

642 Glen Oaks Drive, Leesburg
$299,900
2 Beds ⋅ 2 Baths ⋅ Legacy Leesburg SubDv. ⋅ 34748 Zip Code
Welcome to this beautifully maintained custom Devonshire in the gated 55+ community of Legacy of Leesburg. Thoughtfully designed with expanded living spaces, volume ceilings, and a wall of sliding glass doors, this home offers a spacious, comfortable floor plan that is ready for its new owner. Laminate flooring enhances the main living areas, while bay windows in the breakfast nook and primary bedroom bring in plenty of natural light. The well-appointed kitchen features raised-panel cabinetry with pull-out drawers, upgraded appliances, a walk-in pantry, and glass tile backsplash. An expanded laundry room provides additional storage, a utility sink, and closet space. The spacious primary suite offers an oversized walk-in closet, lanai access, and an en suite bath with custom cherry vanity and true walk-in ceramic shower. The generously sized guest bedroom features an extended closet and convenient access to the guest bath. French doors lead to the den, providing flexible space for a home office, hobby room, or additional sitting area. The enclosed patio, added in 2015, provides additional space to relax and enjoy the Florida lifestyle. And don't overlook the garage! One side of the two-car garage is extra deep, offering plenty of room for a larger vehicle—bring your big truck! It also features a 10x6 workshop area, side service door, window, and pull-down attic storage. Additional features include Hunter Douglas blinds and shades, a Kinetico water system, attic radiant barrier, and foam block insulation. The home has been thoughtfully updated over the years, including four replacement windows in 2016, a generator added in 2017, four additional replacement windows in 2019, a new front door in 2021, and fresh interior paint in 2022. Located in nature-themed Legacy of Leesburg, this very well-maintained home combines comfortable everyday living with access to the community's extensive amenities. Move-in ready and waiting for its next owner—come see everything this inviting home has to offer!

5138 Aurora Drive, Leesburg
$368,000
3 Beds ⋅ 2 Baths ⋅ Royal Highlands Ph 01a SubDv. ⋅ 34748 Zip Code
Recently remodeled 3-bedroom home in the 55+ golf community of Royal Highlands. The rear of the home has a beautiful waterfront view and is positioned next to a large, open green space, providing extra privacy. Updates: Luxury Vinyl floors (2025) with 5-inch base boards, enclosed Florida room with windows (2025), new ceiling fans (2024), new hot water tank (2026), AC unit (2024), roof (2022), garage door opener (2026), garage door sliding screen (2023), new irrigation controller (2024), skylights serviced (2026). Laundry room with a sink and cabinets. (2023) washer/Dryer, kitchen updates, plantation shutters, new LED lighting throughout and a Generac System (Home Generator 2025). Relax and enjoy your pristine lake view from the comfort of your Florida room’s panoramic view! This home has a great layout with views of the lake from the kitchen, dining, living area and Florida room. Unique double master suites and a third bedroom/office. Royal Highlands is a Golf Course Community with 24-hour guard services, clubhouse, restaurant, pickleball courts, indoor and outdoor pools, shuffleboard, tennis, baseball/softball field, all within the community. Waterfront home in top rated 55+ community in Leesburg, Florida. This community has easy access to the Florida Turnpike and is convenient to all the Central Florida attractions.

21932 Royal St Georges Ln, Leesburg
$315,000
3 Beds ⋅ 2 Baths ⋅ Pennbrooke SubDv. ⋅ 34748 Zip Code
Welcome to your own peaceful retreat in Pennbrooke Fairways! This spacious 3-bedroom, 2-bathroom home offers 1,869 sq. ft. of heated living space with soaring ceilings, generously sized rooms, and a bright, airy atmosphere that makes the home feel open and inviting from the moment you step inside. One of the home's standout features is the 250 sq. ft. enclosed lanai overlooking the golf course and pond. Whether you're enjoying your morning coffee, unwinding at the end of the day, or simply taking in the peaceful Florida scenery, this is a space you'll want to enjoy year-round. The home offers plenty of room for both everyday living and entertaining, while the brick-paver driveway adds beautiful curb appeal. Major updates include a new HVAC system in 2025 and roof replacement in 2018, offering added peace of mind for the next owner. Located in Pennbrooke Fairways, a gated 55+ golf community in Leesburg, residents enjoy an active Florida lifestyle surrounded by golf courses, ponds, conservation areas, and beautifully maintained surroundings. Community amenities include three 9-hole golf courses, swimming pools, fitness facilities, tennis, pickleball, bocce, shuffleboard, recreation centers, walking and biking areas, and a wide variety of clubs and social activities. There's even an on-site restaurant, making it easy to meet friends for a meal without leaving the community. Conveniently located near The Villages and Brownwood Paddock Square, you'll have easy access to shopping, dining, entertainment, medical facilities, and everything Central Florida has to offer. Spacious, bright, and perfectly positioned to enjoy tranquil golf course and water views—come discover the relaxed Florida lifestyle waiting for you in Pennbrooke Fairways!

439 Grand Vista Trail, Leesburg
$270,000
3 Beds ⋅ 2 Baths ⋅ Lake Denham Estates SubDv. ⋅ 34748 Zip Code
Move-in ready and built in 2022, this modern 3-bedroom, 2-bath home offers 1,484 square feet of comfortable living in the Lake Denham Estates community. The bright, open-concept layout brings the kitchen, dining area, and generous living room together, creating an inviting space for everyday living and entertaining. At the heart of the home, the kitchen features stainless steel appliances, ample cabinetry, and a center island with breakfast bar seating. Tile flooring extends throughout the main living areas for a clean, cohesive look and easy maintenance. The spacious primary suite offers a private retreat with a walk-in closet and en suite bath featuring a double vanity and large walk-in shower. Two additional bedrooms and a full bath provide plenty of flexibility for family, guests, or a home office. Step outside to the covered patio, offering a comfortable spot to relax and enjoy the outdoors. Lake Denham Estates residents also enjoy access to a community pool and playground. Conveniently located near shopping, dining, and the Florida Turnpike, this newer home combines modern comfort with easy access to everyday essentials and Central Florida destinations.

3916 Brant Place, Leesburg
$325,000
3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Oak Tree Village SubDv. ⋅ 34748 Zip Code
Virtually Staged. “LOCATION LOCATION LOCATION NO CDD's! NO REAR OR FRONT NEIGHBORS!! BEYOND THE LOT, A CREEK! This BEST-LOVED HOME IS FAR from the noise of traffic. Through the canopy of oak trees rests this charming home. Situated behind hole 3 of the Otto Creek Par 72 course, the story of the construction of this home is recounted in a photo album as the original owners have lovingly built it from the ground up. From start to finish PRIDE OF OWNERSHIP MAKES THIS HOME SPECIAL from nail #1, throughout the years, to today. Note the expansive landscaping; gutters and private screened entrance. Even the sprinkler system has been overhauled complete with a new timer (2023/24). NEW ROOF IN 2025. NEW 50 GALLON WATER HEATER IN 2025! New/er appliances include: MICROWAVE in 2026; AC in 2020; Bosch dishwasher in 2021 (5 year warranty); LG refrigerator in 2025 (5 year warranty); Whirlpool stove in 2022 (5 year warranty); washer/dryer in 2022; garbage disposal in 2023. WDO BOND has been maintained with Florida Pest Control. When you enter, you will be confronted by warm ambiance graced with VAULTED CEILINGS of the large Great Room and Dining Combination which foreshadowed the OPEN PLAN that has come in vogue today. Beyond this space, venture into the spacious OFFICE/DEN which makes the LIVING SPACE SO MUCH BIGGER. Journey through the FRENCH DOOR onto the WOODEN DECKED GAZEBO – listen to the hush of the private rear garden. GAZE THROUGH THE GREEN EXPANSE, THIS LOT HAS ABOUT 1/4 ACRE OF REAR GARDEN!! Behind the lot is the Palatlakaha Creek, so the hush is going to be your daily peace! FEEL RIGHT AT HOME in the Kitchen and in the BREAKFAST NOOK, look through the bay window to see how your garden is growing and bask in the gleaming southwest sun. Notice the continuation of the VAULTED ceilings, the 18” tile floors, the beveled countertops and the solid wood cabinets. Continue your tour into the roomy PRIMARY SUITE which offers TWO WALK-IN CLOSETS. This private suite includes a RENOVATED ENSUITE complete with GROUT FREE SHOWER; BENCH SEAT; COMFORT HEIGHT TOILET which can be accessed through a WIDENED PRIVY DOOR; A DRESSING AREA (converted from a garden tub – don’t worry the plumbing is still there); and DIVIDED, RAISED VANITIES. You will enjoy the SPLIT PLAN privacy of MONTEGO model floor plan. Bedrooms 2 and 3 are very spacious. and bedroom 3 is larger and features a DOUBLE DOOR ENTRY (take a look at the floorplan included in the attachments). Bathroom 2 has a new vanity, comfort height toilet, and GROUT FREE tub/shower for easy breeeezzy maintenance. These owners were proud to build this home and had added $$$$$ of upgrades from the builder, and ever since this home has been well maintained in every area including the RECENTLY TREATED FLOORING IN THE OVERSIZED GARAGE and the fresh paint inside. Some Furniture could convey. Plantation is a 55+ community with 24-hour guard gate; two 18-hole golf courses, restaurant, 3 activity centers EACH with pools, fitness facilities, tennis and pickle courts, catch and release fishing, bocce and offers many events and clubs that will keep you very active. MAKE THIS BELOVED HOME YOUR BEST LOVED FOREVER HOME! GOLF CART with new batteries CONVEYS with accepted offer!

25845 Glen Eagle Dr, Leesburg
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