Leesburg Homes with Pool Community Features

Leesburg Homes with Pool Community Features

Welcome to Leesburg, Florida—a charming city nestled in the heart of Lake County, known for its picturesque landscapes and vibrant community spirit. With its rich history, beautiful lakes, and an abundance of recreational opportunities, Leesburg is a hidden gem that offers residents the perfect blend of small-town charm and modern conveniences.

As you explore the city, you’ll discover a variety of local shops, delightful eateries, and cultural attractions that reflect the warm hospitality of its residents. The annual festivals and community events foster a sense of belonging, making it easy to connect with neighbors and create lasting memories.

For those seeking a tranquil lifestyle with a touch of luxury, Leesburg boasts an array of homes with pool community features. Imagine stepping into your own oasis, where you can relax by your private pool or host summer barbecues with friends and family. These communities are thoughtfully designed to enhance your living experience, offering amenities such as well-maintained parks, walking trails, and clubhouse facilities that promote an active and engaging lifestyle.

Whether you’re a first-time homebuyer, a growing family, or looking to retire in a serene environment, Leesburg’s homes with pool community features provide the ideal backdrop for your dreams. With a warm climate year-round, you can enjoy outdoor living to the fullest, making every day feel like a vacation. Come discover the beauty and charm of Leesburg—your perfect home awaits!

Newest Leesburg Homes with Pool Community Features

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

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

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

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

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

25845 Glen Eagle Dr, Leesburg
$370,000
3 Beds ⋅ 3 Baths ⋅ Royal Highlands Ph 01b SubDv. ⋅ 34748 Zip Code
Looking for a LITTLE SLICE OF PARADISE? This beautifully maintained home offers curb appeal, space, comfort and beautiful, Florida-friendly views! Situated on an OVERSIZED (over 1/4 acre), CORNER LOT, this property has been landscaped to LOOK BEAUTIFUL FROM ALL SIDES. This well laid-out Duchess model combines an open floor plan in the living areas, with just enough defined space for privacy and comfort. A SIDE ENTRY GARAGE enhances the curb appeal of this LOVELY HOME and, as you step into the home, views from the living room are of a lush, beautiful backyard nature oasis, comprised of Florida-friendly plantings and a shaded pathway. The spacious living room is the hub of the home. The Kitchen has 42” CABINETS, STONE COUNTERS, a double SS sink, newer appliances, a tiled backsplash, and a solar tube & recipe widows for added natural light. There is a warm, inviting breakfast room just off the kitchen and a dining area on the opposite side of the kitchen. The PRIMARY BEDROOM is located at the rear of the house and has a TRAY CEILING, an AMPLE WALK-IN CLOSET and AN ENSUITE. The private GUEST AREA is located in ANOTHER hallway SEPARATED BY A POCKET DOOR and has a FULL BATH with a TILED TUB/SHOWER COMBO. There are FRENCH DOORS in the Living Room through which you enter the FLEX ROOM that can be used as a THIRD BEDROOM, DEN, TV ROOM, OFFICE, CRAFT AREA ~ whatever you like. The LANAI, which can be accessed by either of two sliding glass pocket doors, is a SPACIOUS addition to the living space of the home and looks out onto the beautiful backyard. The 2 ½ CAR GARAGE WAS TOALLY REBUILT IN 2020 and has drop-down access to the attic, a separate door to the outside, and a window. There is direct access to the laundry room, where you will also find a CONVENIENTLY-LOCATED POWDER ROOM. ROOF REPLACED 2025. UPDATES IN 2020 INCLUDE: INTERIOR & EXTERIOR PAINT, GARAGE REBUILD, WATER HEATER, HVAC, FLOORING, ELECTRCAL PANEL BOX, ATTIC PULL DOWN. This is your opportunity to OWN A HOME WITH LOTS OF ADDED VALUE in this lovely community. Located in the premier GOLF COURSE 55-plus community of ROYAL HIGHLANDS where residents enjoy a full range of amenities, including CABLE & HIGH-SPEED, FIBER OPTIC INTERNET, a GATED entrance with attendants, a GOLF COURSE, a RESTAURANT, tennis, PICKLEBALL, softball, INDOOR & OUTDOOR POOLS, secured RV STORAGE, bocce, shuffleboard, a FITNESS ROOM, a library, arts and crafts, billiards, catch-and-release fishing, and a variety of clubs. There truly is SOMETHING FOR EVERYONE in this vibrant community!

5401 Essex Court, Leesburg
$344,900
3 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 03 Tr A-G SubDv. ⋅ 34748 Zip Code
RENOVATED and ready for new owners | BLOCK and STUCCO exterior construction | 3-bedrooms | 2 full bathrooms | OVER-SIZED garage features 675sf | BRAND NEW Luxury Vinyl Plank flooring throughout | NEW BASEBOARDS and TRIM | Freshly painted interior | NEW fixtures and hardware | Kitchen boasts refaced cabinets, Stainless Steel appliances, including natural gas range, breakfast bar and bench seat | DOUBLE PANE Windows | The Primary Retreat comes with His & Her walk-in closets, fully renovated master bath with tall vanity and cultured marble top, undermount dual sinks and new hardware. Shower (no tub) | French doors lead from the Primary retreat to the Family Room-Sunroom, with loads of natural lighting. | Recessed lighting | Screen enclosed patio located off the family room, with private views of natural Florida. This CONSERVATION LOT with NO REAR NEIGHBOR also has water view of the pond | Washer and dryer convey | Golf cart MAY convey with an accepted offer | SPLIT BEDROOM layout offers two additional bedrooms that share the UPDATED bath | NEW TALL VANITY with undermount sink. | ROOF 2024 | HVAC 2014 | natural gas WATER HEATER 2019 | Electrical panels to be updated PRIOR to sale. Don't wait until it's gone. 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!

27138 Racquet Circle, Leesburg
$165,000
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands Condo Ph A & Aa SubDv. ⋅ 34788 Zip Code
Virtually Staged. Tucked away in a peaceful setting with no rear neighbors and a beautiful wooded backdrop, this charming 2-bedroom home offers the privacy and relaxed Florida lifestyle you've been looking for. Clean, comfortable, and full of character, it's an inviting place to settle in and truly feel at home. Step outside and enjoy the serenity of having woods behind the property, creating a private setting that's perfect for quiet mornings, afternoon relaxation, or simply enjoying nature without another home directly behind you. The home has been well cared for, with a roof replaced in 2019 and HVAC system installed in 2010. Its comfortable layout makes everyday living easy, while the peaceful surroundings add to its warm, welcoming appeal. Located in a wonderful 55+ community, you'll enjoy a quieter residential atmosphere while remaining conveniently close to shopping, restaurants, hospitals, medical facilities, and major roadways. It's a wonderful combination of privacy, convenience, and easy Florida living—all wrapped up in one cute and comfortable home.

21 Aberdeen Circle, Leesburg
$400,000
3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph M Sub SubDv. ⋅ 34748 Zip Code
Resort-Style Amenities & On-Site Conveniences. Exceptional home you will not be disappointed in the 3/2 expanded Key Largo former model home on a premium Golf Course Lot on the 9th hole, overlooking a pond. Concrete block home with stucco exterior, open floor plan. Chef's in the family will be delighted with the oversized kitchen, with snack bar open to the breakfast nook with bay window and slider to the Family room. From there you can go outside on the caged patio area and enjoy your evenings pest free. The Den/Office area is wired for tv and 7.1 surround sound system. Expanded 2 car garage with privacy screen. Forget driving into town for basic errands or a night out. This unique, resident-owned community puts everything you need right at your fingertips:Dining & Pampering: Meet up with friends at the on-site restaurant, or book an appointment at the neighborhood hair and nail salon. Neighborhood Conveniences: Drop off mail or pick up packages directly at the neighborhood on-site post office.State-of-the-Art Fitness Center: Stay healthy and active with top-tier cardio and strength training equipment.Two Heated Swimming Pools: Enjoy year-round swimming, aquatic classes, or poolside relaxation.Endless Active-Adult Sports & RecreationYour toughest daily decision will be deciding which sport or activity to pick first. The extensive recreational facilities include:Championship Golf: Play across beautifully manicured fairways woven directly into the community layout.Dedicated Softball Fields: Join the local league or cheer on your neighbors from the stands.Racquet Sports: Fast-paced competitive play is always waiting at the tennis and pickleball courts.Traditional Lawn Games: Gather for social, outdoor fun at the shuffleboard courts, Bocce ball courts, Lawn Bowling green, or horseshoe pits.Unbeatable Location, When you do decide to venture out, you are perfectly positioned just minutes away from the endless town squares, nightly live entertainment, and dining options at The Villages Brownwood Paddock Square. Exceptional area shopping, diverse restaurants, and leading regional medical facilities are also right around the corner. Don’t miss this rare opportunity to own a piece of paradise in a community that truly has it all!

402 Grand Vista Trail, Leesburg
$365,670
3 Beds ⋅ 2 Baths ⋅ Cedar Landings SubDv. ⋅ 34748 Zip Code
Pre-Construction. To be built. Pre-permitted lot. The Aurora combines elegance with smart design in a stunning single-family home. The open-concept layout features 9’ ceilings throughout, showcasing a gourmet kitchen with a spectacular 7’3” island and modern appliances. An impressive wall of glass floods the dining area with natural light, leading to a patio. The luxurious owner’s suite boasts a tray ceiling, spa-inspired bathroom with seated shower, and generous walk-in closet. With well-proportioned secondary bedrooms, thoughtful storage solutions, and two distinctive elevation options, the Aurora delivers sophisticated main-level living at an exceptional value. Come home to luxury today! Introducing Cedar Landings in Leesburg, Florida! Resort-Style amenities including a zero-entry pool with cabana, a dog park with separate spaces for small and large dogs, a playground, and a 1-acre multi-use green space. 2 miles to the Florida Turnpike, 20 miles to Mt. Dora & Winter Garden, 35 miles to Downtown Orlando, 10 miles to Main Street in Leesburg with local favorite restaurants including The Brick and Barrel Public House, Turners Kitchen, & Prime 3, and 2 miles to The Monarch at Royal Highlands Golf Course. Golfers can play this course and grab burgers and brews at the club's eatery. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.

6374 Cedar Landing Circle, Leesburg
$234,900
2 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 01 SubDv. ⋅ 34748 Zip Code
WATER VIEWS of Lake Egret; one of four catch and release fishing lakes within the community of Highland Lakes. A sought after GATED Active Adult community offering a wealth of amenities. This single-family home awaits new owners and features a screen enclosed front entry that leads to the foyer with ample closet space. | Living and dining room combination | UPDATED KITCHEN with GRANITE countertops, NEW SHAKER style cabinets, stainless appliances less than 4 years old, including a natural gas range, one of three solar tubes for natural lighting throughout the home. | Widened driveway | Gutters | New ceiling fans and fixtures | garage door screens replaced less than one year ago | all new window screens | ROOF 2022 | HVAC with additional filtration system | WATER HEATER 2022 | UPDATED electrical panels | Sunroom over-looking Lake Egret and an open patio beyond. 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!

26616 Evert Street, Leesburg
$388,790
3 Beds ⋅ 3 Baths ⋅ Leesburg Legacy Leesburg Unit 06 SubDv. ⋅ 34748 Zip Code
Welcome Home to Legacy of Leesburg! Looking for that perfect low-maintenance lifestyle in one of Leesburg's favorite 55+ communities? This 3-bedroom, 2.5-bath gem sits on a great corner lot and is ready for its next owner! Step inside and you'll immediately notice the vaulted and tray ceilings that give the home such an open, comfortable feel. The primary suite doesn't disappoint, it comes with its own private bath featuring a garden tub, a separate step-in shower, and a water closet for extra privacy. Love the look of wood but want easy upkeep? You'll appreciate the LVP flooring running through the main living areas, plus ceramic tile in all the right spots. The kitchen is a real highlight with gorgeous granite countertops, plenty of space to entertain, bake, or just spread out for a project. There's also a two-car garage and mature landscaping that gives the whole place a settled, established feel (no waiting years for trees to grow here!). Best of all, the HOA fee takes care of lawn mowing, edging, cable, and internet, so you can spend less time on chores and more time enjoying life. Of course, you can't beat what Legacy of Leesburg offers as a community — a pool, hot tub, billiards room, card room, RV/boat storage (at no additional charge) and plenty more ways to stay active and meet your neighbors. A couple of things to note: the home was updated in 2025, HVAC was replaced in 2025, plumbing was pressure tested and passed inspection, irrigation was given a full update, garage spring was replaced and roof (2012) was recently inspected and reported to be in great condition. This one's got it all — come see it for yourself!

27303 Gingerbread Place, Leesburg
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