Leesburg Homes with Private Pool type

Leesburg Homes with Private Pool type

Welcome to Leesburg, Florida, a charming city nestled in the heart of Lake County that offers a perfect blend of small-town charm and modern conveniences. Known for its picturesque landscapes and vibrant community, Leesburg is an ideal destination for those seeking a serene lifestyle with easy access to urban amenities. With a rich history dating back to the 1800s, this city boasts beautiful parks, lively festivals, and a welcoming atmosphere that makes it feel like home.

One of the most desirable features of homes in Leesburg is the availability of properties with private pools. Imagine basking in the Florida sun, taking a refreshing dip, or hosting unforgettable gatherings with family and friends in your own backyard oasis. Homes with private pools in Leesburg cater to a variety of lifestyles, whether you're a growing family looking for a safe haven for your kids to play or a retiree seeking relaxation and leisure.

The real estate market in Leesburg offers a diverse range of options, from charming single-family homes to luxurious estates, all featuring stunning pool areas designed for both relaxation and entertainment. With the warm Florida climate, a private pool is not just a luxury; it’s a lifestyle enhancement that allows you to enjoy the outdoors year-round.

Explore the beauty and tranquility of Leesburg, where every day feels like a vacation at home. Discover your dream home with a private pool today and embrace the vibrant community and endless opportunities that await you in this delightful city!

Newest Leesburg Homes with Private Pool type

$399,999
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 and spa 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
$275,000
6 Beds ⋅ 3 Baths ⋅ Leesburg SubDv. ⋅ 34748 Zip Code
ESTATE SALE — INVESTOR OPPORTUNITY, HIGHEST & BEST DEADLINE, NO CONTINGENCIES. Historic 1927 fixer-upper on 0.48 acres in the heart of Downtown Leesburg, including an additional buildable lot (1118 W line St former home site — prior impact fees paid may reduce future construction costs). 3,462 sq ft, 6 bedrooms, 3 baths, two full kitchens, large deep pool with expansive back deck. Originally used as a boarding house with separate entrances upstairs and down — incredible flexibility for renovation, multi-generational living, or income potential. Gorgeous original wood floors, soaring ceilings, rare 1927 architecture. Recent partial PVC plumbing update. Being sold by the estate, priced to sell at or above asking. Terms: Listed at $275,000. Seller requires all offers at or above asking price with NO contingencies. Buyers may inspect during the first 7 days from list date; highest and best offer due by Monday August 10, 2026. Closing required within 14 days of contract execution — earnest money due immediately upon acceptance. Sold as-is.

1116 W Line Street, Leesburg
$209,000
2 Beds ⋅ 2 Baths ⋅ Bradford Mobile Estates SubDv. ⋅ 34788 Zip Code
Welcome to this cute as a button, well maintained 2 bedroom 2 bath home that is looking for new owners. Sitting on a half acre lot with mature landscaping you will find a firepit for those cool evenings to sit around and enjoy. A small garden in the back right corner. Behind the outside laundry room you will find hot and cold water available for bathing your furry friend(s) or a quick rinse off after yard work before you jumping into your above ground Coleman pool to cool off from the Florida heat! You will also find all of this behind a chain linked fence where you will find there is room to park your boat, trailer(s), ATV toys or a hobby vehicle you might be working to restore. Located minutes from downtown Eustis, Tavares and Mount Dora where you can go for the festivities the towns have, shopping, fine dining, hospitals and major roadways to get you to Orlando for the theme parks or Ocala for the equestrian shows.

35737 Shelley Drive, Leesburg
$1,295,000
3 Beds ⋅ 3 Baths ⋅ Leesburg Loves Point SubDv. ⋅ 34748 Zip Code
There are homes that offer a place to live, and then there are homes that redefine the way you experience life. Perfectly positioned on the shoreline of Lake Harris, this extraordinary waterfront estate offers an unparalleled opportunity to own a piece of Florida's most coveted boating paradise. As part of the Harris Chain of Lakes, you'll enjoy direct access to more than 76,000 acres of waterways, where every day invites a new adventure, from sunset cruises and championship fishing to waterfront dining and unforgettable days on the water. Completely reimagined in 2020, this home was transformed from the inside out with an uncompromising commitment to craftsmanship, timeless design, and exceptional quality. Every surface, every finish, and every detail was thoughtfully curated to create a home that feels both sophisticated and effortlessly livable. The open-concept floor plan is filled with natural light, creating seamless transitions between elegant gathering spaces that are equally suited for intimate evenings or grand-scale entertaining. Offering 3 spacious bedrooms, 2 1/2 luxurious baths, and a dedicated craft room or home office. The home perfectly balances refined elegance with everyday comfort. Beyond the walls of the home a private dock awaits on the shores of Lake Harris, complete with a touchless boat cover, allowing you to launch effortlessly. Even more impressive, a full-price offer includes the boat, making this a turnkey opportunity to begin living the ultimate lakefront lifestyle from day one. The spectacular swimming pool, recognized as one of the largest residential pools in Lake County, becomes the centerpiece of the outdoor experience. With an impressive nine-foot-deep end, it offers endless opportunities for recreation, entertaining, and resort-style relaxation beneath Florida's endless blue skies. For automotive enthusiasts and collectors, the 1,772 square-foot garage, completed in 2024, is truly extraordinary. Featuring a professional-grade car lift, three independent mini-split air conditioners, and an abundance of space for luxury vehicles, boats, recreational equipment, or an impressive workshop, this is far more than a garage...it's a destination of its own. Luxury extends beyond what meets the eye. A whole-home generator provides confidence in every season, while blown-in foam insulation delivers remarkable energy efficiency, comfort, and quiet throughout the home. Perhaps most remarkable is the value. This exceptional waterfront property is being offered below its recent appraised value, presenting a rare opportunity to acquire a luxury lakefront estate with immediate equity. Unlike many communities, you'll enjoy the freedom of NO HOA, allowing you to embrace your waterfront lifestyle without unnecessary restrictions. This is more than an address. It is sunset cruises from your private dock. It is afternoons exploring miles of pristine waterways. It is elegant entertaining beside one of Lake County's most spectacular residential pools. It is unforgettable celebrations, quiet evenings as the sun melts into shades of gold and crimson across Lake Harris, and the simple luxury of knowing your next adventure is always just steps from your back door. It is a home built not simply to impress, but to be experienced. Properties of this caliber rarely become available. This is a once in a lifetime opportunity to own one of Lake Harris' most exceptional waterfront estates.

1616 Loves Point Drive, Leesburg
$368,900
3 Beds ⋅ 2 Baths ⋅ Legacy Leesburg SubDv. ⋅ 34748 Zip Code
This Home has it All! Do not wait to visit 5121 Aurora Circle. This beautifully maintained Scarborough model has been thoughtfully updated and is move-in ready, with a new roof (2025) and a new A/C system (2022) — major-ticket items already taken care of for the next owner. Tucked on a desirable corner/cul-de-sac lot, the home offers a side-entry, oversized 3-car garage with overhead attic storage, giving it wonderful curb appeal and easy in-and-out access. Beyond the cul-de-sac setting, there are no rear neighbors — just a peaceful conservation view of the St. John's Conservation area right out back, with the community river park and walking trail just steps away for added privacy and a true sense of retreat.Step inside through leaded glass double French doors into a living room with soaring vaulted ceilings, setting the tone for the open, split floor plan that flows throughout. Six solar tubes bring in an abundance of natural light, and three sets of double French doors — including one leading from the primary bedroom — connect the interior seamlessly to the extended, screened paver lanai. Out there, you'll find a swim-current pool and spa/hot tub overlooking the conservation area, plus two ceiling fans on the lanai and one in the garage for year-round comfort. Decorative ceiling fans are also featured in all three bedrooms and the family room.The kitchen is both stylish and functional, with 42" solid wood cabinets, double pull-out drawers for pots and pans, additional pull-outs in the pantry, a built-in desk, a breakfast counter, and ceramic tile flooring. The spacious primary bedroom offers direct lanai access along with two walk-in closets featuring custom-built drawers and shelving. The en-suite primary bath is a true retreat, complete with a jetted garden tub, separate ceramic-tiled walk-in shower, Corian double-sink counters, ceramic tile flooring, and a private water closet.Additional energy-efficient features include foam-filled insulated walls, a radiant roof barrier, a small natural gas heater in the primary bedroom, and double-pane windows throughout — all helping keep utility costs down. A whole-house central vacuum system adds everyday convenience.Located in the sought-after Legacy of Leesburg community, residents enjoy access to tennis, bocce ball, and pickleball courts, a resort-style pool, a state-of-the-art fitness center, a pool hall, library, activity and craft rooms, a softball field, a community hall for gatherings, multiple walking trails, and RV/boat storage. The HOA fee of just $293/month covers lawn care (cutting, edging, and debris blowing), cable, internet, RV/boat storage, and full use of all community amenities. All information recorded in the MLS is intended to be accurate however, it should be independently verified by buyer and their agent.

5121 Aurora Drive, Leesburg
$350,000
4 Beds ⋅ 2 Baths ⋅ Shady Dells SubDv. ⋅ 34748 Zip Code
Take a look at this amazing 4-bedroom/2-bath pool home with 1,903 sq. ft. in the heart of beautiful Leesburg. This home has been lovingly updated with major improvements including a new roof (2023), new windows (2024), a complete kitchen remodel with modern appliances, irrigation system installed in 2024, and a new pool pump (2024). Washer and dryer are also included! This home sits on a large corner lot set back from the road with plenty of room for parking. It features a modern exterior with stacked stone accents and a front patio perfect for entertaining. Inside, enjoy an open layout with a spacious living room, dining room, and a beautifully remodeled kitchen. The kitchen boasts modern appliances, ample storage and prep space, a breakfast nook for extra seating, and opens seamlessly to the dining room. Beautiful wood-planked walls, cathedral ceilings with decorative beams, and tile flooring throughout the main living areas give the home a warm, rustic-meets-modern feel, while the bedrooms are comfortably carpeted. Access the private pool through doors off the kitchen or dining room. There are two bedrooms downstairs, including the spacious master suite with a window seat and a secondary bedroom that opens to the guest bathroom. Upstairs, you’ll find two additional large bedrooms with high ceilings and another full guest bathroom. Outside, relax in your private pool oasis featuring a large deck and bar area for entertaining, plus a refreshing inground pool. A large storage shed provides plenty of space for toys or lawn equipment. This move-in-ready home has something for everyone. Just a short walk from Lake Harris and is conveniently located near shopping and dining, yet tucked away from the hustle and bustle of the city. Recent updates make it truly turnkey

7238 Hillcrest Street, Leesburg
$290,999
3 Beds ⋅ 2 Baths ⋅ Haines Lake Estates SubDv. ⋅ 34788 Zip Code
Virtually Staged. Experience the perfect blend of comfort and style in this beautiful home located in the desirable Haines Lake Estates community. This meticulously maintained 3-bedroom, 2-bathroom residence offers an inviting, open-concept floor plan highlighted by stunning large-format tile flooring that flows seamlessly throughout the entire home. The heart of the home is a well-appointed kitchen featuring stainless steel appliances and a modern aesthetic, perfect for both everyday living and entertaining. Step outside to the screened-in pool enclosure, where the pool is currently filled with sand and covered with turf, creating a unique, low-maintenance outdoor living and recreational space. Should the next owner prefer a traditional swimming pool, the space offers the potential to be converted back, providing flexibility to suit a variety of lifestyles.

11130 Fountain Lake Boulevard, Leesburg
$394,900
3 Beds ⋅ 2 Baths ⋅ Chelsea Park Sub SubDv. ⋅ 34788 Zip Code
Move-in ready, beautifully renovated, and complete with a solar-heated pool—this home delivers the Florida lifestyle without the wait. Located in the desirable, low-HOA Chelsea Park community, this 3-bedroom, 2-bath home blends modern design, upgraded finishes, and a private outdoor oasis rarely found in new construction. Roof new in 2020. A fresh, light, and bright interior welcomes you the moment you step inside. Brand-new luxury vinyl plank flooring flows throughout the expanded living and dining areas, complemented by updated light fixtures that elevate the home’s clean, modern aesthetic. The renovated kitchen is a true showpiece, featuring quartz countertops with a waterfall edge, a spacious island, breakfast bar, updated cabinetry, newer appliances, and stylish finishes that rival today’s new-build design packages. The primary suite offers a peaceful retreat with a new walk-in shower, garden tub, updated ensuite features, a generous walk-in closet, and French doors leading directly to the screened lanai—a perfect blend of comfort and luxury. Step outside to your private outdoor haven—an impressive screen-enclosed, solar-heated sparkling pool, freshly painted pool deck, and a fully fenced backyard with mature landscaping and exceptional privacy. This move-in-ready outdoor living space is a major advantage over new construction, where pools, fencing, and landscaping often require significant additional cost and long wait times. A 2-car garage provides secure parking and additional storage, rounding out the home’s functional design. Located minutes from restaurants, shopping, medical facilities, and everyday conveniences, this modern Florida pool home delivers upgraded design, a private pool lifestyle, and a prime location—an exceptional opportunity that stands out among new-build competition.

33150 Kaylee Way, Leesburg
$1,600,000
7 Beds ⋅ 8 Baths ⋅ Leesburg East Leesburg SubDv. ⋅ 34748 Zip Code
Experience the rare opportunity to own a historic lakefront estate on the coveted Lake Harris Chain of Lakes. Tucked away at the end of a quiet cul-de-sac shared by only a handful of waterfront residences, this remarkable property offers an extraordinary 183 feet of shoreline and breathtaking panoramic views across beautiful Lake Harris. Originally built in 1923, this timeless estate is rich with history and character, having been updated throughout the years while preserving much of its original charm. Now ready for its next chapter, this is a home for someone who appreciates classic architecture, unparalleled waterfront living, and the opportunity to complete its restoration to its full grandeur. The main living area is perfectly positioned on the 2nd level to capture spectacular lake views. Wake each morning to shimmering water vistas from the spacious primary suite, complete with private access to the screened porch, a generous walk-in closet, and an oversized bath. A thoughtful split-bedroom floor plan provides exceptional privacy, while two additional bedrooms each feature walk-in closets and en-suite baths, with one also serving as the home’s guest bath. Designed for both everyday living and elegant entertaining, the formal dining room showcases beautiful built-in cabinetry and French doors opening to a charming front balcony. The inviting family room serves as the heart of the home, where custom built-ins, expansive glass doors, and sweeping lake views create an unforgettable setting. A dedicated office with built-in cabinetry and its own exterior entrance via a spiral staircase offers the perfect space for a home business, private studio, or executive workspace. The versatile first floor expands the home’s possibilities with 4 additional bedrooms (3 do not have closets), three full and two half baths, extensive utility space, and two oversized bonus rooms making the home ideal for multigenerational living, guest accommodations, recreation, hobbies, or potential income-producing opportunities. Outside, the lifestyle is simply exceptional. A sparkling deep pool and spa overlook the lake, surrounded by generous screened lanai space perfect for relaxing, entertaining, or taking in spectacular sunrises and sunsets. Two covered boat docks complete with electric and fresh water provide convenient access to the lake for recreation and enjoyment. A two-car garage, expansive driveway, and deep front yard provide abundant parking and enhance the home’s impressive curb appeal. Offering an unmatched combination of history, privacy, expansive waterfront, and endless potential, this is more than a home—it’s an opportunity to restore and preserve a true Lake Harris legacy for generations to come.

1029 Mellathon Circle, Leesburg
$390,000
3 Beds ⋅ 3 Baths ⋅ Golfview Sub SubDv. ⋅ 34788 Zip Code
POOL HOME ON NEARLY HALF AN ACRE WITH NO HOA! Welcome to this spacious 3-bedroom, 2.5-bath Leesburg home offering 2,496 heated square feet, a private in-ground pool, attached 2-car garage, downstairs primary bedroom, formal dining room, interior laundry room, and a large upstairs loft. The living room features vaulted ceilings, exposed wood beams, and a stone wood-burning fireplace, creating a warm central gathering space. The kitchen offers granite-look counters, a breakfast nook, range, microwave, refrigerator, and dishwasher. Enjoy multiple outdoor living areas, including a covered rear patio, screened upper porch, poolside gazebo, storage shed, fenced yard, mature trees, and peaceful pond views. Conveniently located near US-441, shopping, dining, downtown Leesburg, and area amenities.

9916 Jackson Road, Leesburg
$649,000
3 Beds ⋅ 2 Baths ⋅ Eagles Point Sub SubDv. ⋅ 34788 Zip Code
Your Harris Chain Boating Lifestyle starts here! Experience the best of Florida waterfront living in this beautifully maintained 3-bedroom, 2-bath canal-front home with direct access to Lake Eustis and the renowned Harris Chain of Lakes. Perfectly situated on the edge of Leesburg, this move-in-ready property offers the ideal combination of comfort, convenience, and an exceptional boating lifestyle. Designed for both relaxation and entertaining, the backyard is your private oasis. Enjoy a sparkling inground pool with a tanning ledge, a spacious covered lanai, and a screened enclosure complete with a convenient dog door. The fully fenced yard offers plenty of space for children and pets to play, while the lawn irrigation system draws water directly from the canal, helping keep the landscaping lush while reducing irrigation costs. Water enthusiasts will appreciate the Trex dock with a covered boathouse and boat lift, providing effortless access to boating, fishing, sunset cruises, and all that the Harris Chain has to offer. This home has been thoughtfully updated and meticulously cared for, offering peace of mind with numerous recent improvements. Updates include interior and exterior paint, newer appliances, Trex dock decking, shutters, lighting, and professional landscaping. Major mechanical updates include a new roof (2022), new water heater (2024), new exterior AC unit (2024) and a new state-of-the-art high-efficiency AC air handler, just installed in July 2026. Whether you're searching for a year-round residence, a seasonal escape, or the perfect waterfront retreat, this exceptional canal-front home delivers everything you've been looking for—modern updates, outstanding outdoor living, and direct access to one of Central Florida's most sought-after chains of lakes. Don't miss this rare opportunity to own your own piece of the Harris Chain lifestyle!

12037 Eagle Point Ct, Leesburg
$491,100
3 Beds ⋅ 3 Baths ⋅ 34748 Zip Code
Rare Find in a Fantastic Location! Conveniently located near schools, shopping, restaurants, and charming downtown Leesburg, with easy access to the renowned Harris Chain of Lakes, famous for boating, fishing, and waterfront recreation. Just minutes from The Villages, offering endless dining, shopping, entertainment, and employment opportunities. Quick access to both I-75 and Florida's Turnpike makes commuting a breeze. This well-maintained home offers just under 1,800 square feet of living space with 3 bedrooms and 3 full baths. Inside you'll find a wood-burning fireplace, built-ins, French doors, ceiling fans throughout, a formal living room, dining room, and a spacious family room featuring beautiful pecky cypress accent walls. The kitchen includes stainless steel appliances, a breakfast bar, and a large closet pantry. Major updates include a 2021 HVAC system, new submersible well pump, new iron tank, newer pool pump and filter, and a pool light currently being replaced. The home is also equipped with a water softener, chlorinator, and dechlorinator system. The oversized 16' x 6' utility/laundry room offers abundant cabinet storage and includes the third full bath. Step outside to the impressive 28' x 12' screened porch, perfect for entertaining, family gatherings, or simply enjoying the peaceful country setting. Cool off in the sparkling in-ground pool with an 8-foot deep end, surrounded by a decorative concrete pool deck. The partially fenced yard is ideal for pets and includes a large detached shed plus a covered carport area perfect for storing your boat, tractor, or additional equipment. Bring your boats, RVs, and all your toys! With plenty of room to expand, there's ample space to build a pole barn, detached garage, workshop, or even a second home/in-law suite (buyer to verify zoning and county requirements). So much to offer at an incredible price—don't miss this opportunity!

1112 Caballo Road, Leesburg
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