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

933 Eagles Landing, Leesburg

933 Eagles Landing, Leesburg

2 Beds ⋅ 2 Baths ⋅ Pennbrooke Fairways SubDv. ⋅ 34748 Zip Code

This Move In Ready and Partially furnished 2-bedroom, 2-bathroom residence with NO POPCORN ceilings is located in the desirable 55+ gated golf community of Pennbrooke Fairways. Step inside this OPEN Floorplan to soaring vaulted ceilings, neutral colors and NO CARPET! The eat-in kitchen features tile flooring, a closet pantry, and a large pass-through opening to the living room, making it easy to stay connected with family and friends. The spacious primary suite offers a large walk-in closet and an updated ensuite bathroom complete with a dual-sink vanity and a walk-in shower with built-in seats. The second bedroom is also large in size and easily accommodates a queen bedroom set. The living room can easily accommodate many guests and it has sliding doors that open to a spacious tiled lanai and 14 x 6 concrete patio (perfect for grilling) creating the perfect space to relax or entertain! Major updates include a 2019 roof and a 2018 HVAC, TANKLESS Water Heater, Solar Tubes, All WINDOWS REPLACED in 2020, Vapor Barrier in attic, PLUS a Generac 13 KW WHOLE House generator providing added peace of mind. Enjoy maintenance-free living with a low monthly HOA fee of just $265, which includes lawn care, high-speed internet, cable, and access to an outstanding selection of community amenities. Pennbrooke Fairways features 27 holes of golf, a pro shop, an on-site restaurant, two recreation centers, swimming pools, a fitness center, and countless activities including pickleball, tennis, shuffleboard, softball, horseshoes, water volleyball, and cornhole. Conveniently located near shopping and dining and just minutes from The Villages' Brownwood Paddock Square, this home offers the perfect combination of comfort, convenience, and an active Florida lifestyle.

933 Eagles Landing, Leesburg

4631 Glen Coe Street, Leesburg

4631 Glen Coe Street, Leesburg

3 Beds ⋅ 2 Baths ⋅ Royal Highlands Ph 02-A Lt 1173 Orb 2040 SubDv. ⋅ 34748 Zip Code

Welcome to this Windsor model in the highly desirable 55+ gated community of Royal Highlands! Featuring several significant updates, this home offers comfort, convenience, and peace of mind for its next owner. Major improvements include a NEW ROOF (2023), HVAC SYSTEM (2024), and GENERATOR (2024), along with three replacement windows in 2023 and six additional replacement windows in 2010. Inside, you'll appreciate the attractive solid surface flooring throughout the main living areas, providing a clean, cohesive look and easy maintenance. The kitchen features beautiful stone countertops, while both bathrooms have also been enhanced with stone countertops, adding a touch of elegance throughout the home. One of the home's inviting features is the LARGE ENCLOSED LANAI, offering additional space to relax, entertain guests, or simply enjoy Florida living throughout the year. These desirable features, combined with the major mechanical updates, make this Windsor an appealing choice for buyers looking to enjoy their next chapter without the worry of several big-ticket improvements. Royal Highlands is a resident-owned, gated golf community offering an exceptional variety of amenities and activities. Residents enjoy two swimming pools, one indoor and one outdoor, an 18-hole golf course, restaurant and pro shop, lighted tennis courts, pickleball, bocce ball, shuffleboard, softball, and a driving range with putting practice facilities. The recreation center features a fitness center, billiards, library, activity rooms, and a grand hall hosting social gatherings, entertainment, concerts, and community events. The HOA fee includes Xfinity cable and high-speed internet, along with access to secure RV and boat storage. Conveniently located near the Florida Turnpike, shopping, dining, medical facilities, and Orlando attractions, Royal Highlands offers the perfect combination of an active lifestyle and everyday convenience. Discover the possibilities of this well-appointed Windsor model and start enjoying everything this wonderful community has to offer!

4631 Glen Coe Street, Leesburg

26949 Racquet Circle, Leesburg

26949 Racquet Circle, Leesburg

3 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 03 Tr A-G SubDv. ⋅ 34748 Zip Code

IMMACULATELY MAINTAINED 3-bedroom home in the sought-after GATED community of Highland Lakes. Beautifully UPDATED KITCHEN with dinette space OVER-LOOKING GREENSPACE/CONSERVATION area beyond. NO REAR NEIGHBORS and a peaceful setting with privacy. GRANITE countertops | Island | Subway tile backsplash | Stainless Steel appliances including natural gas range | re-faced cabinetry | NEW Luxury Vinyl Plank flooring (2026). INTERIOR LAUNDRY ROOM with tile flooring and ample cabinetry for additional storage space, includes NEW washer and gas dryer | SPLIT FLOORPLAN | Living and Dining combination | Family Room | Double Florida Room with heat and air wall unit, over-looks serene backyard and conservation land | Whole-house water purification system through Kinetico | ROOF 2016 | HVAC 2016 | Water Heater 2019 | UPDATED electrical (Siemens). 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!

26949 Racquet Circle, Leesburg

109 Camellia Trail, Leesburg

109 Camellia Trail, Leesburg

2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code

Tucked near the Hawthorne Clubhouse, this charming two-bedroom, two-bath retreat offers a welcoming blend of comfort, style, and relaxed Florida living. With attractive vinyl siding, stone-accented landscaping, a long-paved driveway, and a charming picket fence, the home welcomes you with warmth and curb appeal from the very first glance. Step inside to discover a light-filled, coastal-inspired interior that captures the relaxed spirit of the Florida lifestyle. Soft, soothing colors and light-toned vinyl plank flooring create a seamless flow throughout, while reinforced subfloors provide added peace of mind. The atmosphere is bright, comfortable, and effortlessly inviting. The Florida room is a standout feature, offering a sunlit space to savor morning coffee, enjoy a good book, or unwind at the end of the day. Updated windows fill the room with natural light, making it a favorite place to relax and enjoy the easygoing pace of home. Thoughtful updates throughout reflect a true sense of care and pride of ownership. The 2023 HVAC system features a smart touchscreen thermostat for convenient climate control. The 2008 metal roof has been consistently serviced by the same trusted professional, while a 2022 interior electrical panel, the completely re-piped plumbing system, a newer water heater 2018, and new ceiling fans and light fixtures add comfort and convenience. Much of the important work has already been taken care of, allowing you to settle in and enjoy. The kitchen blends style and function with new quartz countertops and a tiled backsplash that adds timeless appeal. Both bathrooms have been refreshed with new quartz countertops, vanities, and medicine cabinets, creating a clean, updated look. The primary suite offers a modern touch with a sliding barn door leading to a walk-in shower, while the guest bathroom features a relaxing tub, ideal for everyday comfort and visiting friends or family. Additional thoughtful details include new cabinet and closet doors, dual storage spaces, a practical utility area, and a separate laundry room. Best of all, this home comes fully furnished, making your transition easy and giving you more time to enjoy the lifestyle you've been looking forward to. Warm, welcoming, and thoughtfully updated, this charming retreat is ready for its next chapter, and ready for you to feel right at home.................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.

109 Camellia Trail, Leesburg

4812 Heron Run Circle, Leesburg

4812 Heron Run Circle, Leesburg

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

AFFORDABLE SITE-BUILT HOME! Needs TLC! Discover an excellent opportunity for affordable Florida living at 4812 Heron Run Circle! This site-built home offers comfortable living spaces, desirable improvements, and a spacious 19' x 12' screened birdcage, perfect for relaxing or enjoying Florida's beautiful weather. A skylight fills the living room with natural light, creating a bright and inviting atmosphere. Notable updates include an air conditioning system installed in 2022 and replacement windows installed in 2014. Whether you're looking for a year-round residence, seasonal retreat, or a place to call your own without breaking the bank, this home deserves a closer look. Don't miss this opportunity to own an affordable site-built home in the Leesburg area. Located in one of Central Florida’s premier 55+ active adult communities. The Plantation at Leesburg boasts 2,820 homes surrounded by manicured lawns, cascading waterfalls, and lush palm trees. Enjoy peace of mind with 24-hour staffed security and a wealth of amenities designed for every interest and budget. Residents have access to three multi-purpose clubhouses, three swimming pools, spring-fed fishing ponds, scenic walking and biking trails, and much more. The community features championship golf courses, tennis, equity memberships, large clubhouses, heated pools, full-time activity directors, over 100 weekly activities, state-of-the-art fitness centers, and is just a short drive to Orlando’s world-class attractions. Please note: property taxes are subject to reassessment after the sale. Schedule your tour today—this home is truly a must-see!

4812 Heron Run Circle, Leesburg

2368 Conestoga Drive, Leesburg

2368 Conestoga Drive, Leesburg

2 Beds ⋅ 2 Baths ⋅ Leesburg East Coachwood Colony SubDv. ⋅ 34748 Zip Code

ENJOY FLORIDA LIVING AT IT'S BEST...WHETHER YOU'RE RETIRED OR JUST KICKING BACK WHY NOT ENJOY THIS INVITING AND STUNNING HOME LOCATED IN THE LOVLEY 55+ COMMUNITY COACHWOOD EAST. MOVE IN READY WITH UPATES THAT INCLUDE A REMODELED KITCHEN, APPLIANCES, PANTRY, GRANITE COUNTER TOPS WITH A BREAKFAST BAR. THIS GRACIOUS AND LOVELY HOME OFFERS 2 LARGE BEDROOMS. GUEST BEDROOM HAS DOUBLE CLOSET SPACE, MASTER SUITE OFFERS EN-SUITE BATH HAS BEEN REMODELED WITH GLASS DOORS TO TILED SHOWER, GRANITE COUNTER TOP, AND A WALK-IN CLOSET. GUEST BATH REMODELED FEATURES LINEN CLOSET, HANDICAP BARS, SHOWER, TUB COMBO. OPEN CONCEPT FLOOR PLAN THAT INCLUDES A LARGE FLORIDA ROOM 12" X 20.5 ALL ENCLOSED, LARGE LIVING ROOM OPENING UP TO A BEAUTIFUL KITCHEN AND LARGE DINING ROOM. FLOORING THROUGH OUT IS VINUL PLANKING. JUST A FEW STEPS AWAY FROM KITCHEN IS AN INSIDE LAUNDRY AREA THAT INCLUDES A STACKABLE WASHER & DRYER. ROOM ENOUGH FOR A FREEZER AND A COUNTER FOR FLOLDING CLOTHES AND/OR STORAGE.

2368 Conestoga Drive, Leesburg

11914 Sussex Hill Way, Leesburg

11914 Sussex Hill Way, Leesburg

3 Beds ⋅ 2 Baths ⋅ Lake Yale Estates SubDv. ⋅ 34788 Zip Code

WELCOME HOME TO LAKE YALE ESTATES — AN OPPORTUNITY TO MAKE IT YOUR OWN! Discover the possibilities in this spacious 3-bedroom, 2-bath manufactured home offering 1,674 square feet of living space in the established Lake Yale Estates community of Leesburg, Florida. The thoughtfully arranged split-bedroom floor plan provides comfortable separation between the primary suite and additional bedrooms. A generously sized living room, dedicated dining area, and centrally located kitchen offer plenty of room for everyday living and entertaining. The kitchen features formica countertops, ample cabinetry, a breakfast bar, and pantry storage. The primary suite includes a walk-in closet and private bathroom with dual sinks, a garden tub, and a separate shower. Two additional bedrooms offer flexibility for guests, hobbies, or a home office. Step outside to an expansive screened porch measuring approximately 20 feet in length, providing a wonderful space to enjoy Florida's year-round outdoor lifestyle. A separate workshop offers additional space for projects and storage, while the two-car carport provides convenient covered parking. ENJOY THE LAKE YALE ESTATES LIFESTYLE! Residents enjoy community access to beautiful Lake Yale, offering opportunities for fishing, relaxing by the water, and enjoying the natural surroundings. Community amenities also include a clubhouse, swimming pool, dog park, and a community dock. The monthly association fee supports a variety of shared amenities and services. This home offers a spacious, functional floor plan with plenty of possibilities for adding your personal touch. With a little attention and creativity, the property presents an opportunity to enhance its existing features and make it uniquely yours. Professional interior and carpet cleaning have recently been completed, providing a starting point for its next chapter. Conveniently located near Leesburg's shopping, dining, medical facilities, and everyday conveniences, this property offers an opportunity to enjoy the Lake Yale Estates lifestyle while creating a home that reflects your personal tastes. Schedule your private showing and discover the possibilities!

11914 Sussex Hill Way, Leesburg

37945 Monticello Street, Leesburg

37945 Monticello Street, Leesburg

3 Beds ⋅ 2 Baths ⋅ Lake Yale Estates SubDv. ⋅ 34788 Zip Code

MOTIVATED SELLER......FULLY FURNISHED, BEAUTIFUL WELL MAINTAINED 3 bedroom/2 bath home in Lake Yale Estates, this turn-key oasis is ready for you to move in and enjoy all that Lake County has for you. The community is on Lake Yale, a beautiful 4,000+ acre lake with great fishing and watersports. This home features a new metal roof (2022) with a large, vaulted ceiling carport, a storage shed/workshop, and a screened in patio for your enjoyment. With 3 large bedrooms that all have walk-in closets and 2 full bathrooms you have plenty of room for family and friends to visit. This home has an open floorplan with vaulted ceilings, a fireplace, built-in desk/shelving in one of the bedrooms, lots of storage, plenty of cabinets and countertop space with an island for cooking and entertaining, and don't forget about the indoor laundry room!!! This golf cart friendly community has so much activity with a heated pool and hot tub, fishing pier, community firepit, and a lovely sandy beach down at the water's edge. Conveniently located near medical facilities, shopping and restaurants with year-round festivals and events at any of the 4 quaint historical downtowns. Welcome Home!

37945 Monticello Street, Leesburg

5853 Princess Caroline Place, Leesburg

5853 Princess Caroline Place, Leesburg

2 Beds ⋅ 2 Baths ⋅ Royal Highlands Ph 01b SubDv. ⋅ 34748 Zip Code

Welcome to one of Royal Highlands’ most darling homes! Perfectly sized at 1,409 square feet under air, this two-bedroom, two-bath Onyx model offers effortless Florida living with a warm, inviting feel. Set on a gorgeous conservation lot, the home provides a front-row seat to native birds and peaceful natural views. Step through the sliding doors to the outdoor paver patio—an ideal place to relax, entertain, or enjoy your morning coffee. New living-room shades add comfort and style. This wonderfully move-in ready property with an optional nearly furnished consideration, this home feels as though it came straight from a Tommy Bahama catalog. Major improvements include a 2018 HVAC system and roof, 2019 windows, and a 2023 water heater. Inside, you’ll appreciate newly installed laminate wood flooring, fresh paint, plantation shutters, an updated primary bath with a glass-enclosed shower, and an updated guest-bath vanity. Additional features include a new garbage disposal, hurricane-tinted protection and privacy glass, as well as an updated backflow and irrigation. The immaculate garage is clean as a whistle and features a new epoxy floor, a newly finished driveway, new washer and dryer appliances, attic storage, a utility sink, and convenient side-yard access. Fresh exterior paint, block-and-stucco construction, and thoughtful updates throughout make this Pringle-built home an exceptional find. The kitchen features granite countertops, Shaker cabinets, and stainless appliances, including a gas range! Royal Highlands is a gated 55+ golf community featuring an 18-hole senior course, a full-service restaurant, courts, clubs, activities, and a large event center for entertainment, dances, and community functions. Residents also enjoy a fitness center, two pools, a library, billiards, and craft rooms. Located approximately 40 minutes from Orlando International Airport, Disney, and Orlando attractions, the community is also convenient to The Villages town squares, historic districts, shopping, restaurants, and both Florida coasts. Come tour this charming home today and discover the Royal Highlands lifestyle!

5853 Princess Caroline Place, Leesburg

27322 Orchid Glade Street, Leesburg

27322 Orchid Glade Street, Leesburg

3 Beds ⋅ 2 Baths ⋅ Leesburg Legacy Unit 03 Lt 259 SubDv. ⋅ 34748 Zip Code

LOCATED IN ONE OF CENTRAL FLORIDA'S PREMIER 55+ COMMUNITIES, LEGACY OF LEESBURG, THIS SPACIOUS CARLISLE MODEL IS PRICED TO SELL. NEW KITCHEN, QUARTZ COUNTERTOPS WITH MATCHING BACKSPLASH, STAINLESS STEEL APPLIANCES. PARKAY FLOORING IN THE GREAT ROOM. PRIMARY BATH HAS A WALK IN SHOWER. SLIDING GLASS DOORS IN THE GREAT ROOM AND PRIMARY THAT LEAD TO THE OUTDOOR SPACE. WHOLE HOUSE GENERAC GENERATOR OFFERS PEACE 0F MIND. LEGACY OF LEESBURG IS A NATURE THEMED COMMUNITY WITH MILES OF WALKING TRAILS ACRES OF CONSERVATION AREA, AND AN ACTIVE LIFESTYLE FOR THOSE WHO ENJOY BEING PART OF A COMMUNITY WHERE FRIENDS MEET FRIENDS. SELL THE LAWN MOWER, THEY CUT THE GRASS WHILE YOUR PLAYING PICKLEBALL, TENNIS, BOCCE OR JUST RELAXING AROUND THE RESORT STYLE POOL.COME SEE WHY SO MANY CALL LEGACY HOME.

27322 Orchid Glade Street, Leesburg

25247 Cranes Roost Circle, Leesburg

25247 Cranes Roost Circle, Leesburg

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

Come and join in the fun in this snowbird friendly neighborhood. Yards are maintained by Golfview HOA. They also powers wash your house twice a year. This community also enjoys their private pool only available to Golfview residents. 2 bedrooms, plus den 2 car garage, front screened porch and back screened porch for relaxing on those warm Florida days. Don't relax too much because there is so much to do in this community. Driveway parties are especially popular. 36 holes of golf and friendly golfers to team up with. On site restaurant is a short golf cart drive away. Enjoy live music on the patio of the Oaks Grille or sing along to karaoke. 3 amenity centers await you with everything from bingo to craft fairs to fitness center, library, dances and 3 heated pools. It is time to join in the lifestyle of the Plantation at Leesburg, a premiere 55 plus guard gated community.

25247 Cranes Roost Circle, Leesburg

1019 Meadowbend Drive, Leesburg

1019 Meadowbend Drive, Leesburg

3 Beds ⋅ 2 Baths ⋅ Pennbrooke Fairways SubDv. ⋅ 34748 Zip Code

3 BEDROOMS | 2 BATHROOMS | BLOCK/STUCCO | PRIVACY IN BACK| ROOF (2023) | WATER HEATER 2022| STAINLESS STEEL APPLIANCES | THERMO PANE WINDOWS| Welcome home to this beautifully maintained custom home in Pennbrooke Fairways, one of Central Florida’s premier gated 55+ GOLF communities. From the moment you pull up, notice the lovely hardscape & updated landscaping as well as the painted driveway & sidewalk. This inviting residence offers privacy, generous living spaces, and the relaxed Florida lifestyle. Step through the elegant leaded-glass front door with side lites into a bright, open floor plan featuring beautiful laminate flooring in the main areas, high ceilings, Updated lighting, and a gorgeous oversized enclosed Florida room (10 x 28) overlooking the private back. The spacious family room flows into the Florida room, creating an ideal setting for everyday living, entertaining, and enjoying the private backyard. The kitchen features abundant cabinetry, stainless steel appliances, a breakfast nook, generous storage, and ample workspace. The thoughtfully designed floor plan includes a spacious primary suite with his and hers walk-in closets, a fully renovated bathroom featuring dual quartz vanities, private water closet and a custom shower that is sure to impress! The second bedroom and full bath/shower combo can easily function as a second primary suite. Additionally, a 3rd bedroom without a closet, featuring double doors can serve as a den or home office. The expansive Florida room overlooking the private backyard area is a true highlight, offering a peaceful setting to enjoy morning coffee, or entertain friends. Additional features include an interior laundry room with a stainless steel utility sink and cabinetry, an oversized two-car garage, a large paver patio area in back, R-38 insulation in home, R30 Insulation in Florida Room, New Carpet in bedrooms (2025) and mature landscaping. Pennbrooke Fairways features 27 holes of golf, a pro shop, an on-site restaurant, two recreation centers, swimming pools, a fitness center, and countless activities including pickleball, tennis, shuffleboard, softball, horseshoes, water volleyball, and cornhole. Conveniently located near shopping and dining and just 6 miles from The Villages' Brownwood Paddock Square, this home offers the perfect combination of comfort, convenience, and an active Florida lifestyle. Enjoy maintenance-free living with a low monthly HOA fee of just $265, which includes lawn care, high-speed internet, cable, and access to an outstanding selection of community amenities.

1019 Meadowbend Drive, Leesburg

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