Leesburg Homes with Pool Community Features

Leesburg Homes with Pool Community Features

Welcome to the charming city of Leesburg, Florida, nestled in the heart of Lake County. Known for its picturesque landscapes and vibrant community spirit, Leesburg offers a delightful blend of small-town charm and modern conveniences. With its rich history, beautiful lakes, and lush parks, it’s an ideal place for families, retirees, and everyone in between.

As you explore Leesburg, you'll discover a variety of recreational activities, from boating and fishing on the sparkling waters of Lake Harris to leisurely strolls through the scenic waterfront parks. The city is home to a vibrant downtown area, featuring unique shops, delightful eateries, and a calendar full of community events that bring residents together. Whether you’re enjoying the annual Leesburg Bikefest or the local farmers' market, there's always something happening in this welcoming community.

For those seeking the perfect home in Leesburg, consider our stunning properties within homes with pool community features. Imagine stepping into your backyard oasis, where you can unwind in your private pool after a long day or host unforgettable gatherings with friends and family. These communities are designed with your lifestyle in mind, offering not only beautiful homes but also amenities such as clubhouses, fitness centers, and walking trails, all surrounded by lush landscaping.

Living in Leesburg means embracing a lifestyle that balances relaxation and recreation. With warm weather year-round, your dream home with a pool awaits, ready to become your sanctuary in this delightful city. Come experience the charm of Leesburg and find your perfect home today!

Newest Leesburg Homes with Pool Community Features

2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg SubDv. ⋅ 34748 Zip Code

* MUST SEE**MANY UPDATES**CONVENIENT TO CLUBHOUSE* You must come and see this nice big home. When you walk in the front door, you'll be wowed by the large, light-filled family room with beautiful windows. Then you'll step into the good-sized living and dining rooms with nice tall ceilings. A built-in buffet in the dining room is great for serving and storage. Entering the kitchen you'll find updated cabinets, granite counter tops, stainless appliances, pantry and eating area. The inside laundry room is just off of the kitchen and leads out to the lanai. One bedroom is a good size with a walk-in closet and updated bath just across the hall. The large primary bedroom features a walk-in closet and updated ensuite bath. All flooring is laminate for easy care. On the outside of the home you'll find covered parking, a large lanai and a separate storage area, with storage closets that remain with the home. This home has a newer roof, newer windows, sinks, lights, appliances etc. all done in 2020. It is truly move-in ready! Buy now so you'll be all set for resort-style living in this wonderful home and community. Plantation is a 55+, gated community golf courses, pools, tennis and pickleball courts, beautiful clubhouse, restaurant and lots of amenities and activities for everyone. There is also boat and RV storage available. Come and see this home today!!!

25047 Bellevue, Leesburg

3 Beds ⋅ 2 Baths ⋅ Leesburg Legacy SubDv. ⋅ 34748 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bath pool home located in the gated 55+ community of Legacy of Leesburg. Offering approximately 2,152 square feet of comfortable living space, this custom Scarsboro model features a desirable split-bedroom floor plan, high ceilings, abundant natural light, and no carpet throughout. The spacious kitchen is designed for both everyday living and entertaining, featuring stone countertops, stainless-steel appliances, a large breakfast bar, center island, built-in desk, GAS cooktop, built-in oven, and a separate dining area overlooking the family room. Formal living and dining spaces provide additional room for hosting family and friends. The generous primary suite is privately positioned on one side of the home and includes direct access to the screened lanai and pool, dual walk-in closets, and a REMODELED en-suite bathroom with a large walk-in shower, updated vanities, stone countertops, tile flooring, mirrors, lighting, sinks, and fixtures. Two additional bedrooms and a guest bathroom are located on the opposite side of the home. Step outside to an expansive screened outdoor living area featuring a private heat controlled SALTWATER pool—the perfect setting for relaxing or entertaining. The backyard offers peaceful water and nature views with no rear neighbors, along with mature fruit trees. The home’s SOLAR system will be paid in full at closing, allowing the new owner to enjoy the benefits without assuming a solar loan or lease. Additional highlights include a 2021 AIR-CONDITIONING system, a 2019 ROOF, an oversized two-car garage, inside laundry room, sliding-glass doors from multiple living areas, and durable hard-surface flooring throughout. Legacy of Leesburg offers an active lifestyle surrounded by scenic wetlands, conservation areas, and miles of walking and biking trails. Community amenities include a resort-style pool and spa, clubhouse, fitness center, aerobics studio, ballroom, billiards, pickleball, tennis, softball, horseshoes, RV and boat storage, and numerous clubs and social activities. HOA services include lawn maintenance, cable, internet, and access to the community recreational facilities. This move-in-ready pool home combines privacy, spacious living, valuable upgrades, and an exceptional community lifestyle.

5519 Aurora Drive, Leesburg

3 Beds ⋅ 2 Baths ⋅ Windsong At Leesburg SubDv. ⋅ 34748 Zip Code

Welcome to 5516 Windsong Oak Drive, an exceptionally upgraded, light & bright 3-bedroom, 2-bath home featuring a huge 3-car garage, a 0.28-acre homesite, & a cozy covered back porch, perfect for morning coffee or evening relaxation. Built in 2020 by Hanover Family Builders, this home offers a rare combination of premium finishes, thoughtful upgrades, & long-term affordability. All appliances, including the washer and dryer, plus all window treatments, are included. The community also features a pool & playground just moments from your front door. Step inside and you'll immediately appreciate the spacious feel created by the 9-foot, 3-inch ceilings, abundant natural light, upgraded porcelain tile flooring throughout the main living areas & bathrooms, designer matte black hardware and fixtures, ceiling fans, stylish lighting with dimmers, and upgraded door hardware. This is far from a cookie-cutter home—every finish has been thoughtfully enhanced. The beautifully appointed kitchen serves as the heart of the home, featuring upgraded cherry cabinetry with 42-inch upper cabinets, elegant angled crown molding, convenient triple-drawer base cabinets, quartz countertops, a Kohler Vault K-15160-CP stainless steel double-basin apron-front sink, garbage disposal, three designer pendant lights, and a microwave vented directly to the exterior. A spacious center island with a breakfast bar overlooks the family room, creating an ideal layout for entertaining. Just beyond, the covered back porch extends your living space outdoors, making gatherings with family and friends effortless. The primary suite is a true retreat, enhanced with two additional windows that fill the room with natural light. The spa-inspired bathroom features a frameless glass shower, an upgraded Kohler electric push-button rainfall shower system, a private water closet, a matching triple-drawer vanity cabinet, a ceiling fan, and custom barn doors. The impressive 8-foot by 6-foot walk-in closet has been professionally customized with built-in shelving and storage, offering exceptional organization. The oversized, insulated 3-car garage is a standout feature, boasting 11-foot ceilings, a 200-amp electrical service upgrade—perfect for EV charging, welding, or a workshop—pre-wiring for the third bay, and a keypad-entry garage door opener. Additional upgrades include a spacious laundry room with a double-basin stainless steel utility sink, an upgraded Samsung washer and dryer with steam features, a whole-house water filtration system requiring no filter changes, and a water softener. The exterior of the home has also been freshly painted, and the upgraded paver driveway and front porch add beautiful curb appeal. The value extends well beyond the upgrades. This home offers an incredible 2.7% FHA transferable interest rate—ask for details. For additional peace of mind, the air conditioning system has been fully serviced with maintenance components replaced and includes a one-year Del-Air warranty. Outdoor enthusiasts will appreciate being just moments from the community's beautiful 30-acre nature preserve, while Pear Park, located less than a quarter mile away, offers hiking trails, pickleball courts, and a dog park. Conveniently located near The Villages, you'll enjoy easy access to premier shopping, dining, golf, and entertainment. 5516 Windsong Oak Drive presents an exceptional opportunity to own a truly upgraded home in one of Lake County's most desirable communities.

5516 Windsong Oak Drive, Leesburg

3 Beds ⋅ 2 Baths ⋅ Leesburg Legacy Of Leesburg Unit 07 SubDv. ⋅ 34748 Zip Code

Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bath pool home in the sought-after 55+ gated community of Legacy of Leesburg! Offering 2,245 sq. ft., this home features an open floor plan, new luxury vinyl plank flooring, and a new A/C. The spacious kitchen includes a gas range and opens to the main living areas, making it ideal for entertaining. Step outside to your private screen-enclosed, solar-heated saltwater pool overlooking a peaceful pond with no rear neighbors. Additional features include plantation shutters, a gas dryer, and a screened garage door. Rare opportunity to assume the seller's low INTEREST mortgage (subject to lender approval and qualification). Enjoy resort-style amenities including a clubhouse, pool, tennis, fitness center, and a full calendar of activities—all conveniently located near shopping, dining, and medical facilities.

27127 Stoney Brook Drive, Leesburg

3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Rosedown Village Lt SubDv. ⋅ 34748 Zip Code

Welcome to your dream home, located at The Plantation at Leesburg! This stunning updated home boasts serene golf course views and BRAND NEW APPLIANCES; which include Refrigerator, Dishwasher and Range in July 2026. As you walk through this beautifully maintained 3 bedroom/2 bathroom home which includes all the furniture, you will enjoy 1,897 sq ft of comfortable living space, while knowing the ROOF was replaced in October 2022, the HVAC in June 2024 and WATER HEATER in June 2024. This home offers an open floor plan with-in the living room/dining room and also has a family room located off of the kitchen; both great spaces for entertaining. The primary suite offers ample space, a walk in closet complete with a private en-suite bath complete with a walk-in shower along with a garden tub. The Plantation at Leesburg is an active 55+ community, with several amenities including 3 club houses, two 18 hole golf courses, 2 fitness centers, pickle ball, bocce ball, shuffleboard, softball/baseball fields, horseshoes, fishing and so much more; along with multiple clubs for you to join. This home truly has it all - style, space and the Florida lifestyle you have been dreaming of. Call for a private showing today.

24403 Amberleaf Court, Leesburg

2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Ashland Village SubDv. ⋅ 34748 Zip Code

Virtually Staged. Welcome to the vibrant lifestyle of The Plantation at Leesburg. This immaculate, move-in ready home offers two bedrooms, two bathrooms, and a generous bonus room ideal for an office, craft space, or den. The kitchen is a true chef’s delight, featuring real wood cabinetry, Corian countertops, stainless steel appliances, and a convenient breakfast bar. The primary suite includes an oversized walk-in closet, dual sinks, a large shower, and direct lanai access. The garage is a hobbyist’s dream — complete with a large workbench, durable epoxy flooring, and space for two vehicles plus a golf cart. Step outside to a spacious covered and screened rear lanai, perfect for relaxed Florida outdoor living. Situated on a roomy, manicured 0.27-acre corner lot with mature landscaping, the home also includes thoughtful updates: attic radiant barrier and foam insulation, a new roof (2022), electric water heater (2023), and HVAC (2017). Life at The Plantation is designed for staying active and engaged. Enjoy two professionally designed 18-hole golf courses, three clubhouses (including the stunning Manor Clubhouse, home to dances and special events), three heated pools, a restaurant and lounge with entertainment, fitness centers, scenic walking trails, fishing, pickleball, bocce ball, shuffleboard, horseshoes, and more than 100 activities and clubs to suit every interest. Conveniently located just minutes from The Villages’ world-class shopping, dining, entertainment, and medical facilities, as well as the 75,000-acre Harris Chain of Lakes for boating and fishing. Orlando’s attractions, international airport, and coastal beaches are approximately one hour away. Schedule your private showing today and experience the lifestyle that makes every day feel like a celebration!

25509 Laurel Valley Road, Leesburg

3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph Q Sub SubDv. ⋅ 34748 Zip Code

Welcome to 842 Old Oaks Lane, a beautifully maintained custom home situated on a private lot in Pennbrooke Fairways, one of Central Florida’s premier gated 55+ communities. With peaceful conservation views and no rear neighbors, this inviting residence offers privacy, generous living spaces, and the relaxed Florida lifestyle. Step through the elegant leaded-glass front door into a bright, open floor plan featuring beautiful hardwood flooring, vaulted ceilings, plantation shutters in all of the bedrooms and expansive views toward the rear of the home. The spacious family room flows into the Florida room, creating an ideal setting for everyday living, entertaining, and enjoying the surrounding natural beauty. Chef inspired kitchen featuring abundant cabinetry, granite countertops, custom backsplash, stainless steel gas appliances, generous storage, and ample workspace. The thoughtfully designed floor plan includes a spacious primary suite with walk-in custom closets, vanity and shower, the second bedroom and custom full bath and shower that can easily function as a second primary suite, plus a separate den or home office with French doors. The expansive Florida room overlooking the conservation area is a true highlight, offering a peaceful setting to enjoy morning coffee, entertain friends, or simply appreciate the privacy and wildlife afforded by having no rear neighbors. Additional features include a 2018 roof, 2012 HVAC system, gas water heater, gas stove, interior laundry room, utility sink and cabinetry, oversized two-car garage, paver driveway and walkway, and mature landscaping. Pennbrooke Fairways offers three golf courses, recreation centers, swimming pools, fitness facilities, tennis and pickleball, clubs, social activities, and on-site dining, all conveniently located near The Villages. 842 Old Oaks Lane offers the space, privacy, and lifestyle that make Pennbrooke Fairways such a special place to call home.

842 Old Oaks Lane, Leesburg

3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Tara View SubDv. ⋅ 34748 Zip Code

HERE IT IS!!!! Premiere golf commumity "THE PLANTATION" with no rear neighbors just beautiful wildlife and sweeping views of the golf course to enjoy while drinking your coffee in the morning or glass of wine in the evening. Nestled in the Tara view area on a quiet cul-de-sac this future home of yours has it all. A verandah, lanai, Huge kitchen, 3rd bedroom can be office or guest room, and the oversized bonus room adds soooo many options for your florida living. Upgrades include Planataion shutters, laminate wood floors, upgraded master bath, screened garage, new roof 2022. The community has amazing resort -style amenities, so dont miss the chance to live the lifestyle you deserve!!!

25102 Meriweather Road, Leesburg

2 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 01b SubDv. ⋅ 34748 Zip Code

DISCOUNTED INTEREST RATE OPTIONS AND NO LENDER FEE FUTURE REFINANCING MAY BE AVAILABLE FOR QUALIFIED BUYERS. SEE LISTING AGENT FOR DETAILS. Welcome to this inviting home in the sought-after gated 55+ community of Highland Lakes, where peaceful water and conservation views create the perfect backdrop for everyday living. A bright and spacious living room welcomes you inside, while the dining area flows into a sunroom, offering the perfect place to relax and enjoy the surrounding scenery year-round. The eat-in kitchen features a breakfast bar, closet pantry, natural gas range, and opens to a cozy den with direct access to the sunroom and views of the shaded backyard. The split-bedroom floor plan provides added privacy for the primary bedroom offering an en-suite bathroom with dual sinks, a walk-in closet, and a walk-in shower. A comfortable guest bedroom, full guest bath, and interior laundry area complete the home's functional layout. Updates include new roof 2024, a/c 2020, water heater 2025, fresh interior paint throughout 2025 and 2026, seamless Pergo flooring with large upgraded baseboards throughout 2025, new water treatment system 2024, new kitchen appliances and washer/dryer combo 2025, new toilets 2025, and new attic insulation installed in 2025, helping improve energy efficiency and reduce monthly power costs. Highland Lakes offers an exceptional lifestyle with indoor and outdoor pools, pickleball, tennis, bocce ball, shuffleboard, fitness center, clubhouse, pool, woodworking shop, library, walking trails, fishing lakes, RV and boat storage, and a full calendar of social activities. Conveniently located near shopping, dining, and everyday conveniences, this home is ready for you to add your personal touches and make it your own. Click the Virtual Tour link to view the 3D walkthrough.

26166 Newcombe Cir, Leesburg

3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Tara View SubDv. ⋅ 34748 Zip Code

Affordable. Move-In Ready. Located in one of Central Florida's most sought-after 55+ golf communities. Welcome to The Plantation at Leesburg, where comfort, value, and an active Florida lifestyle come together. Offering just over 1,700 square feet, this home features a popular 3-bedroom, 2-bath split floor plan with the perfect amount of space—roomy enough to entertain, yet easy to maintain. Step inside to discover vaulted ceilings, an inviting open layout, and abundant natural light. The spacious kitchen offers a convenient eat-in dining area, making it the perfect place to gather for morning coffee or casual meals. The generous primary suite features a walk-in closet and private ensuite bath, while the split-bedroom design provides comfort and privacy for family and guests. An inside laundry room and 2-car garage add to the home's everyday convenience. Relax year-round in the enclosed lanai, an extension of your living space that's ideal for entertaining or simply enjoying the peaceful semi-private backyard and Florida's beautiful weather. Enjoy peace of mind with these major updates already completed for you; a NEW ROOF (2026), HVAC (2021), and lanai WINDOWS (2007)—making this home an exceptional value for buyers seeking affordability, and low-maintenance living. The Plantation at Leesburg is a premier guard-gated 55+ golf community offering two golf courses, three clubhouses, heated swimming pools, fitness centers, pickleball, tennis, softball, shuffleboard, bocce, horseshoes, billiards, an on-site restaurant, and a full calendar of clubs, activities, entertainment, and social events. Conveniently located near shopping, dining, medical facilities, and major highways, you'll enjoy easy access to everything Central Florida has to give. Whether you're searching for a full-time residence or the perfect seasonal retreat, this affordably priced, move-in ready home delivers outstanding value in one of Lake County's most desirable active adult communities. Schedule your private showing today and discover why so many love calling The Plantation at Leesburg home!

25111 Bonnie Blue Court, Leesburg

3 Beds ⋅ 3 Baths ⋅ Plantation At Leesburg Nottoway Village SubDv. ⋅ 34748 Zip Code

Welcome to resort-style living in the highly sought-after Plantation at Leesburg! Nestled on an oversized corner lot in a quiet cul-de-sac, this beautifully maintained 3-bedroom, 2.5-bath home offers an exceptional floor plan featuring two private primary suites, a guest bedroom, an oversized 3-car garage, and fully paid-off solar panels—providing energy efficiency and long-term savings with no solar loan to assume. Step inside to soaring ceilings, abundant natural light, and expansive living areas accented by gorgeous wood flooring. The spacious kitchen features abundant cabinetry, generous counter space, stainless steel appliances, and a breakfast bar that flows seamlessly into the main living areas, making entertaining effortless. The primary retreat offers dual walk-in closets and a spacious en-suite bath complete with dual vanities, a soaking tub, and a separate walk-in shower. A second private suite provides ideal accommodations for guests, extended family, or multi-generational living. Relax year-round in the enclosed Florida room overlooking the peaceful backyard, or enjoy the convenience of the oversized 3-car garage with plenty of space for vehicles, golf carts, storage, or hobbies. Located in the premier 55+ gated community of Plantation at Leesburg, residents enjoy two championship golf courses, multiple swimming pools, tennis and pickleball courts, a fitness center, an on-site restaurant and clubhouse, and a vibrant social calendar filled with clubs, events, and activities. Conveniently located near Florida’s Turnpike, shopping, dining, medical facilities, and all that Central Florida has to offer. With paid-off solar, two primary suites, an oversized garage, and resort-style amenities, this home offers the perfect combination of comfort, efficiency, and an active Florida lifestyle.

4632 Nottoway, Leesburg

2 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 01b SubDv. ⋅ 34748 Zip Code

MOVE-IN READY! *FURNISHED WITH GOLF CART!* New $15,000 Goodman HVAC system with Nest Wi-Fi thermostat (2026), newer roof (2021), brand-new interior paint throughout (2026), new whole-home surge protector (2026), and being sold completely turn-key including the furniture and golf cart! This beautifully maintained end-unit villa offers 2 bedrooms, 2 full baths, a spacious open floor plan, soaring ceilings, a 2-car garage, custom garage screen, epoxy garage floor, workbench, attic storage, and an extended concrete driveway and side walkway. Natural light fills the home, creating a bright and inviting atmosphere. The spacious living and dining areas flow seamlessly into the kitchen, which features ample cabinetry, a breakfast nook, and all appliances included. Enjoy Florida living year-round from two lanais - one screened for enjoying the fresh air and one enclosed for additional living space. The generous primary suite features a walk-in closet, linen closet, and private ensuite bath with a walk-in shower. Guests will appreciate the comfortable second bedroom and adjacent full bath. Located in the highly sought-after 55+ community of Highland Lakes, residents enjoy an incredible array of amenities, including indoor and outdoor pools, a fitness center, clubhouse, ballroom, library, craft room, billiards, pickleball, tennis, bocce ball, shuffleboard, walking trails, fishing ponds, a golf driving range, woodworking shop, and countless clubs, social events, and activities. With thousands of dollars in recent upgrades already completed, this home offers exceptional value and true peace of mind. Simply bring your suitcase and start enjoying the Florida lifestyle! BRING ALL OFFERS!

26740 Cash Court, Leesburg

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