Leesburg Homes with Pool Amenities

Leesburg Homes with Pool Amenities

Welcome to Leesburg, Florida – a charming city nestled in the heart of Lake County. Known for its picturesque landscapes and vibrant community, Leesburg offers a perfect blend of small-town charm and modern conveniences. With its rich history, beautiful lakes, and a plethora of outdoor activities, it’s no wonder that this city is becoming a sought-after destination for families, retirees, and everyone in between.

One of the standout features of Leesburg is its stunning array of homes, many of which come equipped with luxurious pool amenities. Imagine stepping out into your own private oasis, where you can soak up the Florida sun, host family barbecues, or unwind after a long day with a refreshing dip in your pool. These homes are designed for both comfort and entertainment, featuring spacious backyards that provide the ideal setting for relaxation and recreation.

The community is also rich in recreational opportunities, with nearby parks, golf courses, and lakes for fishing and boating. Leesburg’s vibrant downtown area is filled with charming boutiques, delightful restaurants, and local events that foster a strong sense of community. Whether you’re looking to explore the scenic landscapes, enjoy local festivals, or simply relax by your pool, Leesburg has something for everyone.

Discover your dream home in Leesburg today, where poolside living meets the beauty of Florida's natural surroundings. Embrace the lifestyle you’ve always wanted in this welcoming city, where every day feels like a vacation!

Newest Leesburg Homes with Pool Amenities

$239,000
2 Beds 2 Baths Hawthorne At Leesburg A Coop SubDv. 34748 Zip Code
A Masterfully Upgraded Florida Retreat. Welcome to a home that truly stands apart and thoughtfully upgraded to deliver exceptional comfort, craftsmanship, modern functionality, security, and peace of mind. This beautifully enhanced Florida retreat seamlessly blends contemporary sophistication with timeless warmth, creating a home that is as inviting as it is impressive. The expanded Florida room, completed in 2022, is a beautiful coastal-inspired space designed to warmly welcome guests and create an inviting atmosphere for gathering and relaxation. Thoughtful custom window treatments enhance the room’s character while allowing natural light to fill the space. Whether hosting friends, enjoying a quiet afternoon, or simply taking in the relaxed Florida ambiance, this versatile room adds a distinctive layer of charm and comfort to the home. At the heart of the home is a stunning, thoughtfully designed kitchen that makes the most of every inch. A smart, efficient open layout, with an expansive center island, abundant storage drawers, a walk-in pantry, sleek quartz countertops, high-end cabinetry, and luxurious finishes combine style and functionality, making this kitchen equally ideal for everyday living and entertaining. Throughout the interior, from the living room, dining room and bedrooms, luxurious vinyl flooring, upgraded windows, and custom interior doors create a refined and cohesive feel. The inviting bedrooms provide comfortable spaces to relax and unwind, while the beautifully updated bathrooms bring a spa-inspired experience with contemporary vanities and spacious walk-in showers accented by sleek sliding glass doors. The primary suite is a true standout, featuring an extra-large walk-in closet and a certified safe room, providing an added layer of security and protection during severe weather and other natural hazards. The extensive list of improvements provides both beauty and long-term peace of mind, including a new roof and vinyl siding in 2021, a new HVAC system in 2026, and completely updated electrical and plumbing systems. In 2026, the crawlspace was further enhanced with brand-new insulation, a vapor barrier, and ventilation fans to promote improved airflow and moisture management. Step outside and discover even more spaces designed for the Florida lifestyle. The beautiful front porch creates an inviting setting for morning coffee, evening relaxation, or entertaining friends and family. Just steps away, the heated and air-conditioned summer kitchen extends the living and entertaining space, making outdoor gatherings comfortable year-round. A versatile utility room and laundry room with ample storage add even more everyday convenience and functionality. This is more than a home, it’s a masterfully upgraded Florida retreat where beautiful design, coastal-inspired charm, smart functionality, thoughtful improvements, and genuine peace of mind come together. A home designed not only to impress, but to welcome, entertain, relax, and be cherished for years to come.

207 Hawthorne Boulevard, Leesburg

$129,000
2 Beds 2 Baths Hawthorne/Leesburg SubDv. 34748 Zip Code
Be among the first to discover this beautifully refreshed and fully furnished residence offering a surprisingly thoughtful blend of comfort, updates, and everyday livability. While county records reflect an original 1978 build date, the current double-wide manufactured home was replaced in 2004, along with a new carport roof, offering a much different story than the original record may suggest. Step inside to an inviting open-concept layout, where the kitchen flows naturally into the dining, living room and the Florida Room under heat and air, creating an easy setting for both relaxed evenings and entertaining. The kitchen is a standout with a center island and bar seating, stainless-steel appliances, attractive countertops, tiled backsplash, and updated cabinetry. The dining area adds an appealing touch with built-in display cabinetry, perfect for showcasing treasured pieces or creating a distinctive focal point. Throughout the home, beautiful laminate flooring provides a cohesive, contemporary feel, complemented by tile in the kitchen and bathrooms. New subflooring was installed in the living room, dining room, and hallway in 2023. Both bedrooms are generously proportioned and feature dual closets, offering an abundance of storage. The primary bath includes a tiled, enclosed walk-in shower, while the guest bath offers an equally spacious tiled walk-in shower with a sliding glass door. A particularly convenient feature is the guest bedroom’s direct access to the laundry room. The improvements continue beyond the cosmetic. Enjoy exterior vinyl siding, an aluminum roof coated/sealed in 2026, HVAC replaced in fall 2025, an upgraded electrical panel, and a new water heater in 2026. Additional enhancements include double-pane windows installed in 2017 and new awnings in 2025. The utility and laundry room are both under heat and air conditioning, adding valuable year-round functionality. This is a home where the major updates have already been thoughtfully addressed, leaving you free to enjoy the spacious floor plan, comfortable interiors, and inviting outdoor setting. A distinctive opportunity for buyers seeking more than the typical Hawthorne home. Come see the difference for yourself!...........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.

186 Hibiscus Way, Leesburg

$254,900
2 Beds 2 Baths Royal Highlands SubDv. 34748 Zip Code
Set against a peaceful conservation backdrop with no rear neighbors, this beautifully maintained home offers privacy, comfort and an easy resort-style lifestyle. A new roof installed in 2025 adds tremendous value and peace of mind, while select furnishings and all appliances are included, making your move refreshingly simple. The bright and inviting interior features two bedrooms, two full baths and an additional 15-by-11-foot enclosed, air-conditioned Florida room that is not included in the listed living square footage with tile flooring and a ceiling fan. Volume ceilings enhance the open feeling of the living room, where a sliding glass door extends the view into the Florida room. On opposite side, the living space flows naturally into the dining area, creating a comfortable layout for everyday living and entertaining. Laminate and tile flooring provide durability and easy maintenance throughout the home, complemented by knockdown ceilings, bullnose corners, ceiling fans and window treatments. The kitchen is light, crisp and exceptionally functional, with granite countertops, upgraded cabinetry and a convenient dinette for casual meals. The electric range and remaining kitchen appliances are included, allowing the new owner to settle in with ease. The spacious primary bedroom offers a large walk-in closet and a private en-suite bath accessed through a pocket door. The bath includes dual sinks and a walk-in shower with a built-in seat. The guest bedroom is conveniently near the second full bath, which features a tub and shower combination. A linen closet and an additional large hallway closet provide valuable storage. The oversized two-car garage is designed for more than parking. A full screened garage door allows fresh air and natural light to enter while you work at the built-in workbench or take advantage of the generous storage space. The washer, dryer and utility sink are also in the garage and remain with the home. Additional features include a gas water heater, heat pump and an in-ground irrigation system that helps keep the mature landscaping lush and attractive. Beyond the home itself, residents enjoy the exceptional amenities of an active, 24-hour guard-gated community designed to feel like a year-round resort. Enjoy an 18-hole golf course, indoor and outdoor swimming pools, an on-site restaurant, fitness center, tennis and pickleball courts, softball field, library, billiards room and multiple recreation buildings. The impressive Great Hall includes a large dance floor and stage, while an extensive calendar of clubs, activities and social events makes it easy to stay active, meet neighbors and enjoy every day to the fullest. Partially furnished, impeccably maintained and positioned on a private conservation lot, this welcoming home offers the space, convenience and lifestyle you have been waiting for.

21709 King Richards Way, Leesburg

$254,900
2 Beds 2 Baths Highland Lakes Ph 01a SubDv. 34748 Zip Code
Immaculately maintained 2-bedroom PLUS DEN awaits new owners! Back yard lends serene greenspace views and privacy from your neighbors. From the curb appeal to the covered front entry, you're sure to be pleased with the interior layout. Open kitchen and dining room | Luxury vinyl plank and tile flooring (NO CARPETING) | vaulted ceiling | Interior laundry room with wash tub, including washer and dryer | kitchen comes complete with all appliances, including natural gas range | Den/Study/Family Room with views over the backyard, with direct access to the Florida Room | The birdcage/screen enclosure beyond was added in 2020 | The Primary Retreat features Luxury Vinyl Flooring, PLANTATION SHUTTERS, an en suite bath with tile flooring, walk-in closet, shower (NO tub), private commode | SPLIT FLOOR PLAN | Guest Bedroom with walk-in closet | Guest Bath has shower-tub combination, tile flooring and linen closet | ROOF 2019 | HVAC 2012 (serviced regularly) | natural gas WATER HEATER 2021 | UPDATED ELECTRICAL 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!

5614 Austin Street, Leesburg

$415,000
3 Beds 2 Baths Plantation At Leesburg Belle Terre Village L SubDv. 34748 Zip Code
Welcome to this MOVE-IN READY Azelia floorplan (ROOF 2020, A/C 2016) featuring a GOLF CART GARAGE and a propane-heated spa/pool with a water feature overlooking PRIVATE preserve and tree views! This beautifully maintained and thoughtfully upgraded home offers the perfect combination of comfort and privacy for Florida living. Enjoy peaceful views with no rear neighbors from your own spa/pool and outdoor living area—the perfect place to relax and take in the natural surroundings. Inside, you’ll find an open and inviting floor plan featuring 10-foot ceilings, crown molding throughout the living areas, beautiful ceramic tile, and wood-look luxury vinyl flooring. Multiple sliding glass doors and abundant windows bring in natural light while showcasing the beautiful private views. The stunning kitchen is designed to impress with quartz countertops, custom cabinetry with crown molding, under-cabinet lighting, pull-out drawers, soft-close features, stainless steel appliances, a custom hood vented to the exterior, and a stylish backsplash. The spacious layout offers plenty of storage and functionality. The primary suite is a private retreat featuring direct access to the lanai and propane-heated spa/pool area, peaceful views, generous closet space, and a beautifully appointed ensuite bath with a zero-entry glass shower, custom tile work, and upgraded finishes. Additional highlights include double-pane windows, abundant storage, custom cabinetry, epoxy-finished garage flooring, and numerous thoughtful upgrades throughout the home. If you’ve been searching for a beautiful, MOVE-IN READY home with a propane-heated spa/pool with a water feature and truly private preserve and conservation views, this is the one you’ve been waiting for! Plantation at Leesburg offers an active 55+ lifestyle with 3 resort-style pools, 2 fitness centers, craft and art rooms, a billiards room, library, and so much more! Additional amenities include pickleball, tennis, basketball, horseshoes, bocce ball, and a wide variety of planned activities to keep you active and enjoying every day. Conveniently located less than 30 minutes from The Villages, approximately one hour from Orlando International Airport, Disney, and Universal, and less than two hours from the beaches on either coast. Discover the best of 55+ living at Plantation at Leesburg -where every day brings the opportunity to explore, relax, and enjoy the natural beauty that surrounds you! Call today for your private tour!

5524 Belle Terre Drive, Leesburg

$359,900
3 Beds 2 Baths Highland Lakes Ph 2-A SubDv. 34748 Zip Code
COMPLETE INTERIOR RENOVATION of this BLOCK and STUCCO 3-bedroom home is ready for immediate occupancy! Screen enclosed front entry leads to the open and airy floor plan. ALL NEW fixtures and hardware |KNOCK-DOWN ceiling texture | 6-inch baseboards throughout |DOUBLE PANE WINDOWS | Kitchen features QUARTZ countertops and backsplash, NEW Shaker Style CABINETS with 42-inch upper's, complete with crown molding for a finished look, stainless hardware, soft-close hinges, deep undermount stainless steel sink, stainless appliances, including natural gas range for the chef in the family, and an island with breakfast bar, quartz countertop and more cabinet storage. | Luxury Vinyl Plank flooring throughout the home | freshly painted | Primary Retreat with sliding glass door accessible to the covered lanai, vaulted ceiling, His & Her walk-in closets and an en suite bath featuring seamless tile flooring that flows right into the shower. Updated hardware, bench seat, lighted niche and seamless glass shower door. His and Her separate tall vanities include QUARTZ countertop, Shaker Style cabinetry, and touch mirrors that dim the lighting to create that special ambiance. Soft-close hinges on all cabinets, including medicine cabinets. And let's not forget to mention the Primary bathroom also features His and Her private commodes. Fit for a Queen and her King! | An interior laundry room boasts ample closet storage space, washer and dryer hookup and laundry tub. | Split bedroom layout offers two additional bedrooms that share the guest bath, featuring QUARTZ countertop, tall Shaker cabinet, tile flooring, large linen closet, tub and shower combination and direct access to the enclosed lanai. | Covered screen enclosed lanai has new screens, tile flooring and dual ceiling fans. | ROOF 2026 | HVAC 2021 | WATER HEATER 2019 | Siemens electrical 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!

5606 Laver Street, Leesburg

$269,000
2 Beds 2 Baths Pennbrooke Phase 1k, Unit Iii SubDv. 34748 Zip Code
LOOKING FOR THE PERFECT FLORIDA RETIREMENT HOME? Welcome to 32901 Enchanted Oaks Lane, located in the desirable 55+ community of Pennbrooke Fairways in Leesburg! This well-maintained 2-bedroom, 2-bath home with a den/study and open Florida/sitting room offers an open, comfortable floor plan and is ready for its next owner to move right in and start enjoying the Florida lifestyle. Step inside and you will immediately notice the fresh, neutral interior, vaulted ceilings, abundant natural light and NO CARPET! The open living and dining areas provide plenty of room for entertaining family and friends, while the den/study offers additional flexible space for a home office, hobby room or guest space. The kitchen features an abundance of wood cabinetry, generous counter space, tiled backsplash, stainless steel appliances, breakfast bar and adjoining dining area surrounded by windows that bring in plenty of Florida sunshine. The spacious primary suite includes a private en-suite bath with barn doors and large walk-in closet, while the second bedroom and guest bath with no tub provide comfortable accommodations for visiting family and friends. One of the home's great features is the enclosed Florida room, providing additional space to relax, read a book, entertain or simply enjoy your morning coffee. Outside, the home's attractive landscaping, decorative edging, irrigation, gutters and spacious driveway contribute to its clean and welcoming curb appeal. ROOF 2021, A/C 2018, HOTWATER HEATER 2022 new ceiling fans throughout along with many other upgrades (see the attached list) add to the home's list of valuable features. And did we mention NO MORE MOWING? Lawn mowing is included through the HOA! Pennbrooke Fairways offers the active Florida lifestyle so many buyers are searching for, with golf, swimming pools, clubhouse, fitness and activity facilities, tennis, softball and numerous recreational and social activities. The community is conveniently located near The Villages, shopping, dining, medical facilities and entertainment, while its Central Florida location provides convenient access to Orlando-area attractions, airports and both Florida coasts. Whether you are looking for a full-time Florida residence or the perfect place to enjoy your retirement years, 32901 Enchanted Oaks Lane is ready to welcome you home. Schedule your private showing today! WHO YOU WORK WITH TRULY MATTERS — LET US SHOW YOU WHY.

32901 Enchanted Oaks Lane, Leesburg

$275,990
2 Beds 2 Baths Lake Denham Estates SubDv. 34748 Zip Code
Virtually Staged. WHOLE-HOUSE GENERATOR, FULLY FENCED BACKYARD, TWO ADDED SKYLIGHTS, TRIPLE SLIDERS, AND A SCREENED LANAI make this beautifully maintained 2020-built villa stand out in Lake Denham Estates! This 2-bedroom, 2-bath villa also offers a versatile den/flex room that can be used as a home office, guest space, reading room, or hobby area. The open-concept layout is bright and inviting, with two skylights added after construction to bring in even more natural light. The kitchen features solid-surface countertops, a gas range, and smart-home technology, while the spacious primary suite includes dual vanities and two walk-in closets. Triple sliding glass doors open to the screened lanai and fully fenced backyard, creating a wonderful extension of the living space for relaxing, entertaining, pets, or enjoying the Florida sunshine. A whole-house generator provides added peace of mind, and the attached two-car garage offers additional storage and convenience. Lake Denham Estates offers a welcoming community atmosphere with amenities that include a resort-style pool and playground. Conveniently located just off Highway 27 in Leesburg, close to shopping, dining, medical facilities, entertainment, and major roadways. With its thoughtful upgrades, outdoor living space, excellent storage, and move-in-ready condition, this villa offers features that are hard to find in the community. Come see what makes this home different!

29229 Armoyan Boulevard, Leesburg

$275,500
2 Beds 2 Baths Leesburg Arlington Ridge Ph 1-C SubDv. 34748 Zip Code
MAINTENANCE-FREE FLORIDA LIVING! 2 BED/2 BATH HOME WITH HOA COVERING ROOF, EXTERIOR PAINT, LAWN CARE, IRRIGATION, CABLE & INTERNET! Start living the Florida dream with worry-free living whether you’re looking for a year-round residence or the perfect winter retreat! Fall in love at first sight with this immaculate home, where comfort, thoughtful upgrades, and an active lifestyle come together. Step inside to a bright, open living space featuring luxury vinyl flooring throughout the main living areas and a layout designed for easy everyday living and entertaining. The kitchen overlooks the living room, dining area, and bonus/flex room and features upgraded soft-close cabinetry, stainless steel appliances, a stylish backsplash, upgraded granite countertops, and recessed lighting. The split-bedroom floor plan offers privacy, with the primary suite tucked away at the rear of the home and featuring ultra-soft upgraded carpeting with thick plush padding, two closets, and an ensuite bath with a walk-in shower, dual-sink vanity, upgraded cabinetry, and granite countertops. Just outside the primary suite is a versatile bonus/flex room ready to fit your lifestyle—home office, den, craft room, reading retreat, or whatever works for you! On the opposite side of the home, Bedroom #2 features the same plush upgraded carpeting and is conveniently located near the guest bath with a tub/shower combination, upgraded cabinetry, and granite countertops. A large walk-in utility closet provides additional storage and convenience. When Florida’s cooler weather arrives, relax on the screened-enclosed lanai —the perfect spot for morning coffee or unwinding at the end of the day. The extended driveway leads to a 1-car garage with a built-in workshop, golf cart parking area, and 30-amp electrical hookup. And when you’re ready for some fun, you may have a hard time deciding what to do first! Start your morning at the driving range or enjoy a round on the 18-hole championship golf course, then take advantage of the fitness center, resort-style pool, lap pool, restaurant, pub, arts & crafts, card room, billiards, library, tennis, pickleball, community cinema, and more. Best of all, the HOA helps make life easy by including exterior painting, roof, lawn care, irrigation, internet, and cable—giving you more time to enjoy the lifestyle you came to Florida for! As if that weren’t enough, LOCATION, LOCATION, LOCATION! HERE’S WHERE THE FUN REALLY BEGINS! Fill your days with an 18-hole championship golf course, driving range, resort-style pool, lap pool, fitness center, restaurant, pub, arts & crafts, card room, billiards, library, tennis, pickleball, community cinema, and more. Your biggest decision may simply be what to do first! And while you’re enjoying everything Florida living has to offer, the HOA takes care of the roof, exterior painting, lawn care, irrigation, cable, and internet. LESS MAINTENANCE. MORE FUN. MORE FLORIDA! Plus, you’re approximately 5 minutes from Downtown Leesburg, minutes from the Florida Turnpike, and less than an hour from Orlando. Whether you’re searching for your full-time Florida home or the perfect seasonal getaway, this is your opportunity to spend less time worrying about home maintenance and more time living the lifestyle you came to Florida to enjoy!

27001 White Plains Way, Leesburg

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