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, renowned for its picturesque landscapes, vibrant community, and a lifestyle that seamlessly blends relaxation with recreation. With its rich history and welcoming atmosphere, Leesburg offers a unique blend of small-town charm and modern amenities, making it an ideal place for families, retirees, and everyone in between.

One of the standout features of Leesburg is its abundance of homes with pool community amenities. Imagine coming home to your own private oasis, where you can unwind and cool off during those warm Florida days. These communities not only provide luxurious swimming pools but also foster a sense of camaraderie among neighbors, creating an inviting environment for social gatherings and family fun.

As you explore Leesburg, you'll discover beautiful parks, scenic lakes, and an array of outdoor activities. The city's location provides easy access to the stunning Harris Chain of Lakes, perfect for boating, fishing, and water sports. For those who enjoy a round of golf, the area boasts several well-maintained courses, ensuring that every golf enthusiast finds their perfect match.

The downtown area is vibrant and full of life, featuring quaint shops, delightful cafes, and cultural events throughout the year. Whether you’re strolling through the local farmer's market or enjoying a sunset at one of the lakeside parks, Leesburg invites you to experience its warm community spirit.

If you’re searching for a home that offers both comfort and a sense of belonging, look no further than Leesburg's homes with pool community features. Dive into a lifestyle that combines relaxation, recreation, and community connection in this wonderful city!

Newest Leesburg Homes with Pool Community Features

$103,000
2 Beds ⋅ 2 Baths ⋅ Molokai Co-Op SubDv. ⋅ 34788 Zip Code
Welcome to 107 Diamond Head Drive in the 55+ resident-owned Molokai community! This 2-bedroom, 2-bathroom home offers a pond view and an enclosed Florida room providing additional flexible living space. Enjoy the amenities of this active community, including a swimming pool, shuffleboard court, clubhouse, and much more. Conveniently located in Leesburg near shopping, dining, recreation, and everyday conveniences. Whether you're looking for a comfortable full-time residence or a place to enjoy the Florida lifestyle, this home offers the opportunity to become part of an established 55+ resident-owned community.

107 Diamond Head Drive, Leesburg
$204,900
2 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 01b SubDv. ⋅ 34748 Zip Code
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 ⋅ Plantation At Leesburg Nottoway Village SubDv. ⋅ 34748 Zip Code
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 ⋅ Royal Highlands Ph 01b SubDv. ⋅ 34748 Zip Code
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
$279,900
3 Beds ⋅ 2 Baths ⋅ Lake Denham Estates SubDv. ⋅ 34748 Zip Code
Virtually Staged. LIKE-NEW HOME WITH HIGH CEILINGS, QUARTZ COUNTERTOPS & FULLY FENCED BACKYARD! Swim in the Community Pool. This beautifully maintained home shows like new and is move-in ready! Great curb appeal starts with attractive landscaping, a paver driveway and walkway, and continues inside with high ceilings, fresh interior paint and beautiful tile flooring throughout the main living areas..... The spacious kitchen features quartz countertops, stainless steel Whirlpool appliances, a natural gas range, stainless steel sink and a large built-in pantry. The open floor plan provides plenty of room for everyday living and entertaining, with access to a covered rear patio overlooking the fully fenced backyard with 6-foot vinyl privacy fencing. A convenient gate in the backyard provides direct access to the community mailboxes and outdoor fitness area with exercise equipment..... The split-bedroom floor plan offers a private Primary Suite at the rear of the home with carpeting, a large walk-in closet and ensuite bath featuring dual vanities, beautiful tile and a walk-in shower. Two additional bedrooms are located on the opposite side of the home along with a second full bath with tub/shower..... Additional features include a natural gas water heater, large laundry room, hallway storage, keyless entry and pavers on the driveway, walkway and covered rear patio. Lake Denham Estates offers community amenities including a swimming pool, playground, outdoor fitness area and more. A backyard gate provides convenient direct access to the community mailboxes and an outdoor fitness area. Conveniently located close to shopping, restaurants, medical centers and everyday services. Meticulously maintained, freshly painted and ready to go — this one feels almost brand new!

29923 Anahid Dr, Leesburg
$229,900
2 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 01 SubDv. ⋅ 34748 Zip Code
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
$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. 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 ⋅ 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
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