Leesburg Homes with Pool

Leesburg Homes with Pool

Welcome to Leesburg, Florida, a charming city nestled in the heart of Lake County, where picturesque landscapes meet a vibrant community spirit. Known for its stunning lakes and lush greenery, Leesburg offers a unique blend of small-town charm and modern conveniences. With a rich history dating back to the late 1800s, this welcoming city boasts a variety of recreational activities, from boating and fishing on the Harris Chain of Lakes to exploring the scenic walking trails in local parks.

One of the highlights of living in Leesburg is the opportunity to enjoy beautiful homes with pools—perfect for soaking up the Florida sun! Imagine stepping out into your own backyard oasis, where you can unwind after a long day or host gatherings with family and friends. These homes with pools not only provide a refreshing escape but also enhance your lifestyle, offering a private retreat for relaxation and entertainment.

The real estate market in Leesburg is diverse, featuring a range of properties that cater to various tastes and budgets. Whether you’re seeking a cozy single-family home or a spacious residence with modern amenities, you’ll find plenty of options that include inviting swimming pools, perfect for those warm Florida days.

In Leesburg, you’ll experience a friendly community, excellent schools, and easy access to shopping and dining. With its beautiful homes and delightful atmosphere, Leesburg is not just a place to live; it’s a place to thrive. Come discover your dream home with a pool in this enchanting city!

Newest Leesburg Homes with Pool

$129,900
2 Beds ⋅ 2 Baths ⋅ G5118443 MLS
Welcome to easy Florida living in this beautifully maintained 2-bedroom, 2-bath home offering 1,236 square feet of comfortable living space. Bright, inviting, and filled with natural light, this home has been thoughtfully cared for and is ready for its next owner. The spacious living room is highlighted by impressive panoramic windows that create an open, airy feel and provide plenty of natural light. Fresh interior finishes, attractive ceiling fans, updated light fixtures, and beach-inspired touches give the home a relaxed Florida style. One of the standout features is the enclosed Florida room with glass windows and heat, providing additional year-round space for relaxing, entertaining, hobbies, or enjoying your morning coffee. The well-maintained kitchen offers a functional layout with plenty of room for everyday meal preparation. Both bedrooms are comfortably sized, with the primary suite featuring a private bath with walk-in shower. The guest bathroom includes a tub, offering added convenience for visitors. A large laundry room provides valuable additional storage space. Outside, the long driveway, vinyl siding, and refreshed exterior add to the home’s curb appeal. Additional improvements include newer windows, a well-maintained roof-over, and a 2022 HVAC system. Whether you are searching for a full-time Florida residence or a seasonal getaway, this home offers comfort, functionality, and plenty of space to enjoy. Located in Hawthorne at Leesburg, a gated, resident-owned 55+ cooperative waterfront community, residents enjoy an impressive selection of amenities and activities. The $397 monthly maintenance fee includes water, sewer, lawn mowing, private emergency services, and secure storage for RVs, boats, and trailers. The community clubhouse features seating for approximately 550, a full-time program coordinator, and more than 100 activities, along with a hospitality lounge, card rooms, craft and fine arts rooms, billiards, fitness center, and library. Residents can also enjoy an outdoor geothermal-heated pool, two enclosed therapeutic pools, excellent fishing, beautifully landscaped grounds, lakes with illuminated fountains, and a relaxing gazebo. Hawthorne’s private, marina offers 120 boat slips with direct access to the Harris Chain of Lakes and beyond.

408 Palo Verde Drive, Leesburg
$309,900
3 Beds ⋅ 2 Baths ⋅ G5118394 MLS
Virtually Staged. Tucked on a cul-de-sac in the gated 55+ community of Royal Highlands, this expanded Balmoral offers a peaceful conservation setting with no rear neighbors. The 3-bedroom, 2-bath home has 1,559 square feet of living space and solid surface flooring throughout, including engineered hardwood and ceramic tile. The eat-in kitchen features a breakfast bar, closet pantry, built-in microwave and recessed lighting. It opens to a spacious great room with sliding doors to the screened lanai, where vinyl stacking windows and a convenience bar with a refrigerator make the space easy to enjoy in every season. An adjoining patio offers another spot to relax outdoors and take in the natural setting. The primary suite includes a walk-in closet, jetted tub, separate shower and dual-sink vanity. An inside laundry room leads to the two-car garage, while plantation shutters and a screened front entry add to the home’s appeal. All appliances, the water heater and the HVAC system have been replaced within the last five years. Royal Highlands offers indoor and outdoor pools, pickleball and a convenient Leesburg location near the Florida Turnpike.

4512 Inverness Drive, Leesburg
$499,900
3 Beds ⋅ 4 Baths ⋅ G5118361 MLS
Virtually Staged. Welcome to this truly one-of-a-kind custom home, privately positioned at the end of a quiet cul-de-sac in the gated 55+ community of Legacy of Leesburg. Offering an impressive 3,362 square feet of living space, this spacious residence features three bedrooms, three-and-a-half bathrooms and an oversized lot backing to a peaceful conservation area. Beautiful curb appeal begins with mature landscaping, Colorado flagstone accents and an attractive water feature. Inside, the thoughtfully designed floor plan places the primary living areas on the first floor and provides generous space for both comfortable everyday living and entertaining. The kitchen features 42-inch oak cabinetry with crown molding, pull-out drawers, stainless-steel appliances, granite countertops, a center island and abundant storage. The oversized primary suite is a relaxing retreat with two walk-in closets, dual raised vanities, a garden tub and a remarkable wraparound walk-through shower with dual showerheads. An additional Florida room with dedicated air conditioning offers the perfect setting to unwind while enjoying the natural surroundings and visiting wildlife. Residents of Legacy of Leesburg enjoy a resort-style heated pool, clubhouse, fitness center, pickleball, tennis, bocce, softball, walking and biking trails, and a private riverfront nature park. This exceptional home offers space, privacy and an active Florida lifestyle—schedule your private showing today!

5353 Treasure View Way, Leesburg
$520,000
5 Beds ⋅ 4 Baths ⋅ G5118289 MLS
Welcome to your dream oasis in the desirable Lagomar Shores community of Leesburg! Built in 2017, this stunning contemporary two-story, single-family residence has been beautifully elevated to feature an expansive 5-bedroom, 3.5-bathroom floor plan boasting 3,185 square feet of living space. Complete with a 2-car garage featuring a direct interior entrance into the home, a dual AC system offering customized climate control for each floor, and spectacular indoor-outdoor upgrades, this home is designed for premium Florida living. Enjoy enhanced privacy and style with a newly added, fully screen-enclosed front stone veneer entrance opening into a bright, welcoming foyer. Inside you’ll find a highly desirable, open floor plan that flows effortlessly from the entrance into the main living areas, making it perfect for both daily living and hosting guests. Arrive home easily through the direct interior entrance from the 2-car garage, leading into the main floor spaces near a dedicated downstairs laundry room that adds ultimate functional convenience. The Gourmet Dream Kitchen integrates perfectly into the open layout, offering high-end finishes including a spacious granite breakfast bar counter island perfect for casual dining and complete with a built-in sink, dishwasher, and additional built-in cabinets for maximize storage. The crown molding, 42-inch custom cabinetry, recessed lighting, premium double built-in oven, glass stove top, convenient closet pantry, and stainless-steel appliances make this a great gathering space for hosting gathering. Your Retreat to the downstairs master bedroom, is complete with an elegant tray ceiling and tall windows that flood the room with gorgeous natural lighting and leads to a luxurious ensuite bathroom that features dual sinks, a separate toilet closet for privacy, and an over-sized walk-in shower equipped with multiple shower heads, including a premium rain shower head. Inside you will also find an oversized walk-in closet for all your clothing needs. As you ascend the beautifully remodeled wooden staircase you will come upon your entertainment Hub with a massive 27x16 loft area that serves as an ideal gaming arena, media room, or casual hangout space. The upstairs layout features 4 spacious bedrooms and 2 full bathrooms—including a clever Jack and Jill bathroom accessible directly from two of the bedrooms. Back downstairs, Step through dual French doors into a brand-new resort-style retreat. The centerpiece is a stunning, custom-engineered free-form Gunite inground swimming pool measuring 17' wide by 38' long with a rare 9' deep end. The pool features natural flowing curves, multiple serene stone waterfalls, custom leveled edge designs, a salt chlorinator ready for easy saltwater conversion, and custom recessed lighting for magical night swims. The entire outdoor space is fully protected by a massive, soaring 50' by 40' screen enclosure standing 16' tall, offering unparalleled volume and openness. Call today for your private tour!

2125 Amor Way, Leesburg
$525,000
3 Beds ⋅ 3 Baths ⋅ O6445328 MLS
Picture your mornings starting on your own private, second-story balcony, sipping coffee as the sun rises over the quiet woods behind your home. Located in one of Leesburg’s premier communities, this beautiful property welcomes you with a picture-perfect paver driveway, a cozy front porch, and the effortless upkeep of premium Rhino Shield exterior paint. Inside, warm, real hardwood floors flow through an open and airy layout. Step into a light-filled gourmet kitchen where baking and hosting feel effortless. Crisp double ovens stand ready for holiday meals, while a generous central island and breakfast bar invite friends to pull up a stool and chat while you cook. This beautiful space flows naturally into a formal dining room, making it easy to transition from casual meal prep to elegant candlelit dinners. Downstairs also features a cozy fireplace in the living room and a bright, dedicated office that could easily become a fourth bedroom or a creative studio. The layout offers a rare and luxurious setup with two separate primary suites. The main-floor suite is perfect for guests, while the upstairs serves as your ultimate personal sanctuary, complete with a charming reading loft. When it's time to unwind, step out into the massive, screened-in lanai. With a dramatic two story screen and a backyard that backs right up to the trees with no rear neighbors, it feels like your own private, peaceful oasis. Welcome home.

5384 Aurora Drive, Leesburg
$284,900
3 Beds ⋅ 2 Baths ⋅ O6442541 MLS
Welcome to Lake Denham Estates, where this immaculate 3-bedroom, 2-bath Jemison offers a USDA 0% down financing option for qualified buyers, along with seller-offered closing cost assistance. Beautiful curb appeal welcomes you into 1,645 square feet of thoughtfully designed living space. A spacious entry and wide hallways lead to an open living and dining area overlooking the expansive, fully fenced backyard. The kitchen offers abundant cabinet space, a large walk-in pantry, and a gas range. A dedicated laundry room, ample storage, smart home features, a sprinkler system, and a tankless gas water heater add everyday convenience. The desirable split floor plan gives everyone room to spread out. One bedroom and a full bath sit in their own wing, while another bedroom with French doors makes a wonderful guest room or home office. The spacious primary suite features a walk-in closet and an en suite bath with double sinks, a private water closet, and a walk-in shower. Out back, the covered lanai is the perfect place to relax and enjoy the generous yard. Lake Denham Estates offers a community pool overlooking a conservation area and a playground, with shopping, dining, and major Central Florida routes nearby. Whether you’re searching for a primary residence, second home, or investment property, come see all this home has to offer. Schedule your private showing today and ask about the available financing and closing cost options!

29496 Caspian Street, Leesburg
$599,000
3 Beds ⋅ 2 Baths ⋅ O6444786 MLS
Welcome to 2314 N. Griffin Drive, a private Lake Griffin retreat situated on approximately one acre with 100 feet of lakefront and beautiful water views throughout the property. Lake Griffin is part of the Harris Chain of Lakes, offering outstanding opportunities for boating, recreation, and bass fishing right from your backyard. This inviting home captures the relaxed Florida lifestyle with terra cotta tile flooring in the main living area, terrazzo flooring in portions of the home, and a spacious kitchen featuring light stone granite countertops, a center island, breakfast bar, a new refrigerator, and a newer gas range. The home also features gas central heat. Large windows and thoughtfully positioned living spaces take advantage of the lake views, while the screened patio provides another peaceful place to relax and enjoy the natural surroundings. Outside, the 20’ x 40’ screened pool and cabana are enclosed by a full screen cage and positioned to overlook the water. The private dock features a double-deck boathouse with two boat hoists, an upper viewing deck, and a new electrical panel and breakers, creating an ideal setting for boating, fishing, wildlife watching, and enjoying the scenery of Lake Griffin. A new roof was installed in June 2026 and includes a transferable warranty for the next owner, along with a professional soft wash at the five-year mark and application of a protective sealant at the ten-year mark through the roofing company. Additional improvements include fresh paint, updated stucco, and a newer garage door opener. The property is served by two wells, with one dedicated to irrigation and the second supplying the home. Household water is filtered through a water-conditioning system. Although the property feels like a secluded waterfront escape, it remains conveniently located near numerous restaurants, shopping, entertainment, medical services, and everyday conveniences in the Leesburg area. With direct access to the Harris Chain of Lakes, exceptional bass fishing, generous lake frontage, a private dock, pool, and approximately one acre of land, this property offers a distinctive combination of waterfront living, privacy, recreation, and Florida charm.

2314 N Griffin Drive, Leesburg
$204,900
2 Beds ⋅ 2 Baths ⋅ G5117682 MLS
RENOVATED and ready for immediate occupancy! This single-family Villa with courtyard entrance is PRICED TO MOVE - Don't wait! Furniture negotiable | 2-bedroom split lay out with 2 full bathrooms | NEW HVAC (August 2026) | OVER-SIZED garage features 274sf with screened entry | NEW stainless appliances | washer and dryer included | GRANITE countertops in kitchen | PORCELAINE PLANK TILE FLOORING throughout and nearly new carpet and pad in bedrooms | NEW BLINDS |NEW FRONT DOOR and hardware | Fresh interior paint | Covered enclosed rear patio has NEW PERGO luxury vinyl plank flooring AND NEW vinyl WINDOWS scheduled for install, making this currently screen enclosed space ideal for year-round enjoyment. | Skylight and solar tube add loads of natural lighting | Dining and living room combination with vaulted ceiling, 8-foot sliding glass door to access the covered lanai. The Primary Retreat features makeup vanity with single sink, walk-in closet, shower-tub combination and skylight. This split bedroom floorplan boasts the Guest Bedroom at the front of the home, over-looking the courtyard, features dual closets and direct access to the guest bath; featuring updated vanity and shower-tub combination. Entire interior freshly painted April 2025 | Roof 2024 | HVAC 2026 | Water Heater approximately 6 years new | Updated electric panel | Highland Lakes is a gated 55+ community situated in Central Florida just south of Leesburg & offers residents the following amenities: Recreational Clubhouse with two swimming pools; indoor (heated) & outdoor, a softball field complete with concession stand, an indoor arena with a stage for comm. events, complete kitchen, billiard/ping pong rm., 4 tennis courts (2 courts are lighted), 1 indoor tennis court, 8 lighted shuffle board courts, bocce ball courts, 2 outdoor and 4 indoor pickleball courts, 7 horseshoe pits, covered picnic pavilion with picnic tables & grills to barbeque, library, meeting/card room, exercise room/fitness, craft room, golf driving range, RV/boat storage (included in HOA) & has 260 spaces on a secured lot (fenced & lockable), a Craftsmen building/woodworking shop (homeowners can join the club for only $12 annually and use any/all tools available), there's also a Nature Trail within the community & seven lakes scattered throughout Highland Lakes; 4 are used by residents for catch & release fishing! Don't wait............. call now to schedule your private tour!

26032 Newcombe Circle, Leesburg
$357,000
2 Beds ⋅ 2 Baths ⋅ G5118174 MLS
Virtually Staged. REFINED FLORIDA LIVING in The Plantation at Leesburg! Beautifully updated and situated on a landscaped CORNER LOT in desirable Nottoway Village, this 2BR/2BA + STUDY home offers 2,051 sq ft, an ENCLOSED FLORIDA ROOM and expansive SCREENED LANAI. With extensive recent improvements, this home shows beautifully with a LIKE-NEW, MOVE-IN READY feel! The interior features CROWN MOLDING, and a neutral color palette ready to complement any décor. NEW 2026 LUXURY VINYL PLANK flooring throughout the main living areas and bedrooms. The UPDATED KITCHEN shines with NEW QUARTZ countertops, freshly painted cabinetry with SOFT-CLOSE doors/drawers and new hardware, NEW Samsung stainless RANGE, DISHWASHER AND REFRIGERATOR, NEW SINK and FAUCET, center ISLAND, pantry, and abundant storage. A SEPARATE DINING ROOM just off the kitchen provides the perfect setting for easy entertaining. The spacious PRIMARY SUITE features a CUSTOM WALK-IN CLOSET and private ensuite with dual vanities, makeup area, garden tub and separate shower. The GUEST BEDROOM and adjoining STUDY share a convenient JACK-AND-JILL BATH, creating flexible space for guests, a home office or additional living needs. Relax in the nearly 27-ft ENCLOSED FLORIDA ROOM, then step outside to the LARGE SCREENED CAGE—an inviting place to enjoy Florida evenings and gaze at the stars. Major improvements include NEW AC 2026, NEW WATER HEATER 2026 and NEW ROOF 2024, plus IMPACT WINDOWS in select areas, freshly painted interior, solar board attic barrier and foam insulation in the cinder blocks. The EXTENDED 2-CAR GARAGE features an epoxy floor, cabinetry and WORKBENCH. Enjoy the sought-after 55+ GOLF COMMUNITY lifestyle with pools, fitness, pickleball, tennis, golf, clubhouses, restaurant and activities. BEAUTIFULLY UPDATED, LIKE-NEW & MOVE-IN READY—schedule your private showing today!

24445 Madewood Avenue, Leesburg
$525,000
4 Beds ⋅ 4 Baths ⋅ G5118222 MLS
LAKEFRONT. POOL. PRIVACY. AND A TRUE CUSTOM HOME. Tucked away on a quiet cul-de-sac in the desirable 55+ community of Royal Highlands, this impressive 3,318 sq. ft. custom home offers 4 bedrooms, 4 baths, a home office/bonus room, an oversized 3-bay garage and beautiful views of Lake Monarch. Major improvements include a NEW ROOF in 2025, TWO HVAC SYSTEMS replaced in 2020 & 2022, 8 NEW WINDOWS in 2026 plus 2 additional windows replaced in 2024. A transferable termite bond provides additional peace of mind. From the moment you enter, the spacious, open design draws your eye through the great room to the pool and sparkling lake beyond. Multiple pocket sliding doors open the living space to the screened pool and lanai, creating an exceptional setting for entertaining or simply enjoying peaceful Florida mornings and gorgeous sunrises over the water. The expansive great room features a gas fireplace surrounded by custom built-in display shelving. The bright, open kitchen offers newer appliances, abundant cabinetry and counter space, an extended breakfast bar and an enormous walk-in pantry. Just off the kitchen, a second large screened porch creates another inviting outdoor living and dining space overlooking the private backyard setting with mature oaks. The primary suite is truly unique, featuring generous closet space and separate his-and-hers bathrooms connected by a shared walk-through shower. Two guest bedrooms share a convenient Jack-and-Jill bath, while an additional guest bedroom provides flexibility for family and visitors. The light-filled office/bonus room enjoys beautiful views and could easily serve as a craft or hobby room. Even the oversized laundry room was designed with functionality in mind, offering extensive cabinetry, counter space and a utility sink. And then there’s the garage! The oversized 3-bay configuration includes dedicated golf cart space, an enclosed workshop and a rear roll-up door providing convenient access for lawn equipment and projects. Royal Highlands offers an active Florida lifestyle with indoor and outdoor pools, pickleball, tennis, softball, fitness and recreation facilities, clubs, entertainment, billiards, library and more. The community is also home to the Monarch Golf Club and its restaurant. With substantial recent improvements, exceptional indoor and outdoor living spaces, a private pool and a premium Lake Monarch setting, this is anything but the typical Florida home.

5409 Essex Court, Leesburg
$279,900
3 Beds ⋅ 2 Baths ⋅ G5117929 MLS
Virtually Staged. LIKE-NEW HOME WITH HIGH CEILINGS, QUARTZ COUNTERTOPS & FULLY FENCED BACKYARD! Swim in the Community Pool. This beautifully maintained home shows like new and is move-in ready! Great curb appeal starts with attractive landscaping, a paver driveway and walkway, and continues inside with high ceilings, fresh interior paint and beautiful tile flooring throughout the main living areas..... The spacious kitchen features quartz countertops, stainless steel Whirlpool appliances, a natural gas range, stainless steel sink and a large built-in pantry. The open floor plan provides plenty of room for everyday living and entertaining, with access to a covered rear patio overlooking the fully fenced backyard with 6-foot vinyl privacy fencing. A convenient gate in the backyard provides direct access to the community mailboxes and outdoor fitness area with exercise equipment..... The split-bedroom floor plan offers a private Primary Suite at the rear of the home with carpeting, a large walk-in closet and ensuite bath featuring dual vanities, beautiful tile and a walk-in shower. Two additional bedrooms are located on the opposite side of the home along with a second full bath with tub/shower..... Additional features include a natural gas water heater, large laundry room, hallway storage, keyless entry and pavers on the driveway, walkway and covered rear patio. Lake Denham Estates offers community amenities including a swimming pool, playground, outdoor fitness area and more. A backyard gate provides convenient direct access to the community mailboxes and an outdoor fitness area. Conveniently located close to shopping, restaurants, medical centers and everyday services. Meticulously maintained, freshly painted and ready to go — this one feels almost brand new!

29923 Anahid Dr, Leesburg
$229,900
2 Beds ⋅ 2 Baths ⋅ G5118163 MLS
Virtually Staged. BEAUTIFULLY RENOVATED VILLA OFFERING EASY, LOCK-AND-LEAVE FLORIDA LIVING! Whether you're searching for a full-time residence or a seasonal getaway, this thoughtfully updated villa offers the perfect combination of comfort, convenience, and low-maintenance living. With more than $50,000 in improvements, much of the work has already been done for you! Step inside to discover a bright, inviting interior featuring updated flooring throughout, fresh paint, modern lighting, and a beautifully remodeled kitchen. Four skylights fill the home with natural light, while a natural gas fireplace adds warmth and character to the living area. One of the home's standout features is the enclosed lanai, thoughtfully incorporated into the living space to create additional room for entertaining, a home office, or a comfortable retreat for visiting guests. The updated primary bathroom features a raised vanity, and the home's extensive improvements continue with a new roof and skylights (2022/2023), HVAC system, electrical panel (2024), garage door (2024), and water heater (2025). Even the garage has received attention with recessed lighting, providing flexibility for additional seasonal use. Step outside to enjoy your own private courtyard, an inviting space for morning coffee or relaxing Florida evenings. LOVE TO TRAVEL? THIS IS THE LOCK-AND-LEAVE LIFESTYLE YOU'VE BEEN LOOKING FOR! The HOA takes care of many exterior maintenance responsibilities, including irrigation and termite protection, includes a roof replacement reserve, AND OFFERS FREE BOAT AND RV STORAGE—an added convenience that's perfect for enjoying the Florida lifestyle. Spend less time worrying about home maintenance and more time enjoying everything Central Florida has to offer. With extensive renovations, flexible living spaces, and the convenience of villa living, this home is ready for your next chapter. Pack your bags and start enjoying the Florida lifestyle!

5440 Rosewall Circle, Leesburg
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