Leesburg / Haines Creek Homes with Pool

Leesburg / Haines Creek Homes with Pool

Welcome to the enchanting region of Leesburg, nestled in the heart of Lake County, Florida. Known for its picturesque landscapes and vibrant community spirit, Leesburg offers a perfect blend of small-town charm and modern amenities. With its proximity to the stunning Harris Chain of Lakes, residents enjoy an abundance of recreational activities, from boating and fishing to hiking and biking along scenic trails. The area is also rich in history, featuring quaint shops, delightful dining options, and a variety of cultural events throughout the year.

One of the standout features of homes in this region is the availability of properties equipped with private pools. Imagine stepping into your own backyard oasis after a long day, where you can unwind and soak up the Florida sun. Homes with pools in Leesburg and the nearby Haines Creek area provide the ideal setting for relaxation and entertainment. Whether you're hosting a summer barbecue, enjoying a peaceful morning swim, or simply lounging with a good book, a private pool enhances your living experience in this beautiful region.

The real estate market in Leesburg is diverse, offering everything from charming single-family homes to spacious estates, many of which boast stunning pool designs. With a welcoming community and a laid-back lifestyle, it's no wonder that families, retirees, and everyone in between are drawn to this vibrant area. Discover your dream home with a pool in Leesburg and embrace the Florida lifestyle you've always envisioned!

Newest Leesburg / Haines Creek Homes with Pool

33916 S Sabal Way, Leesburg
$349,900
3 Beds ⋅ 2 Baths ⋅ G5119763 MLS
PRICED TO SELL! BEAUTIFULLY UPDATED 3-BEDROOM, 2-BATH POOL HOME WITH A 2025 ROOF! Enjoy the benefit of two years of thoughtful renovations in this inviting Leesburg home, where extensive improvements and a private heated pool create an exceptional opportunity to enjoy the Florida lifestyle. Major updates include a new roof in 2025, attic insulation in 2024, bedroom flooring in 2024, and a new pool heater in 2025. Fresh landscaping around the pool and Zoysia sod, both added in 2025, enhance the outdoor setting and curb appeal. Split floor plan, new tile flooring in front of entryway laundry room, Beautifull walk in tile main bathroom. Key West themed outdoor oasis awaits you. Fresh exterior stucco and a wood burning fireplace. Enough space for 2 boats or recreational vehicle with fenced perimeter of your home. New high efficiency water heater in 2025 and a new cooling system. These highlights are just the beginning—request the complete improvement list to appreciate everything the owners have accomplished. Inside, three bedrooms and two full bathrooms provide comfortable space for everyday living and visiting guests. Outside, your private pool offers the perfect setting for a refreshing swim, weekend entertaining, or a relaxing evening at home. The new pool heater extends your swimming season and adds another reason to love your backyard retreat. Conveniently located near shopping, restaurants, the mall, and everyday essentials, this home puts Leesburg’s conveniences within easy reach, with The Villages to the north. An unexpected change in family circumstances means the owners must relocate, giving the next buyer the opportunity to enjoy the improvements they have worked so hard to complete. Schedule your private showing and discover the details that make this pool home stand out!

33916 S Sabal Way, Leesburg
35132 Silver Oak Drive, Leesburg
$340,000
3 Beds ⋅ 2 Baths ⋅ G5119789 MLS
Florida Pool Home – Relaxed Living at Its Best! Welcome to this inviting 3-bedroom, 2-bath pool home, where comfort, charm, and the laid-back Florida lifestyle come together beautifully! Nestled in a hidden gem of a neighborhood, this property offers the added benefits of NO HOA and a community well, helping keep water costs low. Enjoy the best of Florida living with your own private pool, perfect for cooling off on those warm summer days. For the ultimate relaxation, unwind in the impressive hot tub valued at over $20,000! Inside, you'll find a comfortable and thoughtfully designed floor plan featuring a generous primary bedroom and spacious living areas. The beautiful solid wood kitchen cabinets add timeless charm and create a welcoming space for cooking and entertaining. Make the most of the Florida room, an ideal spot to enjoy your morning coffee, relax with a good book, or entertain guests year-round. Wood flooring throughout the common areas and wood-look vinyl flooring in the bedrooms create a warm, inviting atmosphere. Additional features include: **New AC installed in 2023**RV hookup outside**Generator hookup in the garage**New pavers in the backyard**Private pool and relaxing hot tub**No HOA **Community well for lower water costs Whether you're looking for a peaceful retreat or the perfect place to entertain, this home offers the comfort, features, and Florida lifestyle you've been searching for. Don't miss the opportunity to make this wonderful pool home your own!

35132 Silver Oak Drive, Leesburg
11241 Pine Ridge Road, Leesburg
$369,000
4 Beds ⋅ 3 Baths ⋅ O6453678 MLS
Discover the potential of this unique courtyard-style 4-bedroom, 2.5-bath home offering 2,260 sq ft on an oversized waterfront lot in Umatilla. The private courtyard features a pool surrounded by patio space, creating a great setting for outdoor enjoyment. The spacious family room offers a vaulted, beamed ceiling, brick fireplace, and sliding glass doors opening to the pool area. A separate formal living room provides additional gathering space, while the large open kitchen features abundant cabinetry and counter space with a breakfast bar overlooking the dining area. Enjoy the scenic setting beneath beautiful, mature live oaks, with a covered dock along the canal. Additional features include an attached 2-car garage and a separate workshop. A distinctive property with generous space, a private pool, and waterfront appeal, ready for its next chapter. All information recorded in the MLS is intended to be accurate but cannot be guaranteed, buyer advised to verify. Listing agent has no knowledge of property or disclosures.

11241 Pine Ridge Road, Leesburg
11250 Lake Drive, Leesburg
$349,900
3 Beds ⋅ 2 Baths ⋅ G5119563 MLS
YOUR FLORIDA POOL HOME WITH BEAUTIFUL LAKE VIEWS — PET FRIENDLY, FENCED BACKYARD & NO CARPET! Welcome to 11250 Lake Drive in Leesburg, Florida! Looking for the perfect Florida home where you can relax by your own SCREEN-ENCLOSED FIBERGLASS SWIMMING POOL, enjoy beautiful views of Fountain Lake, and have a FENCED BACKYARD FOR YOUR FOUR-LEGGED FAMILY MEMBERS? Look no further! This inviting three-bedroom, two-bath home offers beautiful hardwood and ceramic tile flooring throughout — ABSOLUTELY NO CARPET! Enjoy the perfect combination of easy-care flooring, a pet-friendly backyard, your own private swimming pool, and peaceful lake views! SCREEN-ENCLOSED FIBERGLASS SWIMMING POOL! Step outside into your own private Florida paradise! The beautiful fiberglass swimming pool features a smooth, durable surface that’s generally easier to clean and maintain than many traditional pool finishes. The screened enclosure helps keep leaves, insects, and debris out of the water, allowing you to spend less time cleaning and more time relaxing! Whether you’re swimming, entertaining friends, enjoying weekend barbecues, or simply unwinding poolside, you’ll love the peaceful views of Fountain Lake! PET-FRIENDLY FENCED BACKYARD! Your four-legged family members will love having their own outdoor space! The backyard features attractive vinyl PVC privacy fencing, creating a wonderful setting for pets to play, outdoor entertaining, gardening, or simply enjoying Florida’s beautiful weather. A fenced backyard, private pool, and scenic lake views make this outdoor space especially inviting! BEAUTIFUL HARDWOOD & CERAMIC TILE FLOORING — NO CARPET ANYWHERE! Enjoy the warmth and character of beautiful hardwood floors complemented by attractive ceramic tile throughout the home. These easy-to-maintain surfaces are especially appealing to pet owners and anyone who appreciates the convenience of a carpet-free home! AIR-CONDITIONED FLORIDA ROOM WITH BEAUTIFUL POOL & LAKE VIEWS! One of the home’s most enjoyable features! Imagine sipping your morning coffee while overlooking your sparkling swimming pool and the peaceful waters of Fountain Lake. This enclosed, air-conditioned Florida room provides a comfortable place to relax, entertain guests, or enjoy the beautiful scenery throughout the year! THREE BEDROOMS & TWO BATHROOMS! The desirable split-bedroom floor plan provides added privacy and a comfortable arrangement for everyday living, family gatherings, and entertaining. LOW HOA — ONLY $375/YEAR! Enjoy all the benefits of Florida living with an affordable annual homeowners association fee! THE FLORIDA LIFESTYLE YOU’VE BEEN LOOKING FOR! Whether you’re searching for a full-time residence, a seasonal Florida getaway, or a place where you and your pets can enjoy the sunshine! FIBERGLASS SWIMMING POOL! FENCED BACKYARD! PET FRIENDLY! HARDWOOD & TILE FLOORS! NO CARPET! BEAUTIFUL FOUNTAIN LAKE VIEWS! Why settle for an ordinary backyard when you can enjoy your own private swimming pool overlooking beautiful Fountain Lake? DON’T MISS THIS OPPORTUNITY — SCHEDULE YOUR PRIVATE SHOWING TODAY!

11250 Lake Drive, Leesburg
9525 Starling Loop, Leesburg
$329,490
4 Beds ⋅ 3 Baths ⋅ O6453657 MLS
Virtually Staged. Pre-Construction. To be built. The Seaton II is the perfect single-family home for growing families and first-time buyers. Step from your front door or two car garage into a light, airy living area with an open kitchen overlooking the great room- complete with access to private patio or large covered lanai for those who enjoy outdoor activities or entertaining guests alike! On the other side of this ideal setup lie three bedrooms, two bathrooms, a walk-in laundry room and more! The secluded primary suite has all you need in privacy; dual sinks, spacious closet plus extra linen storage make it feel like nothing else matters but restful comfort! Get ready to settle down somewhere special – come see why this 2,001 square foot new construction could be just what you've been looking for! *Photos are from a similar home.

9525 Starling Loop, Leesburg
10240 Barrington Court, Leesburg
$430,000
3 Beds ⋅ 2 Baths ⋅ G5119392 MLS
Poolside afternoons, dinner on the screened patio, and room to bring the boat—this three-bedroom, two-bath Leesburg home brings Florida living into focus. With inviting indoor gathering spaces and a fully fenced backyard anchored by a swimming pool, the property offers plenty of ways to enjoy time at home. A spacious kitchen and two dining areas set the stage for everything from casual breakfasts to celebratory dinners. There’s room to gather, serve, and entertain, with outdoor living spaces adding another dimension. The primary suite holds an unexpected bonus: an extra room ready to become a workout space, hobby studio, nursery, home office, or something entirely your own. This versatile space adds possibilities beyond the bedroom, while two walk-in closets provide generous storage. The adjoining bathroom features dual sinks, a walk-in shower, a separate toilet area, and direct porch access. Two additional bedrooms complete the accommodations. Step outside and make the most of the sunshine. Cool off in the pool, settle into the screened patio with your morning coffee, or take dinner outdoors. The fenced backyard brings these spaces together for a relaxed extension of the home. A garage and carport add utility, with additional space for boat or RV parking. Shopping, dining, downtown Leesburg, Mount Dora, and Lake Harris boating destinations round out the location’s appeal. From the possibilities of the primary suite’s bonus room to afternoons spent poolside, this home offers space to create your own version of Florida living.

10240 Barrington Court, Leesburg
11914 Sussex Hill Way, Leesburg
$195,000
3 Beds ⋅ 2 Baths ⋅ G5119129 MLS
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
32919 Indian Woods Drive, Leesburg
$385,000
3 Beds ⋅ 2 Baths ⋅ O6440191 MLS
Virtually Staged. Enjoy the best of Florida living in the established Silver Lake Forest community of Leesburg, where this spacious single-story POOL HOME offers a bright, functional layout, inviting outdoor spaces and a large .29 ACRE LOT! Recent improvements include a NEW POOL PUMP (2024), NEWER ROOF (2023), and SEPTIC DRAIN FIELD (2023), along with an UPDATED A/C & WATER HEATER, plus LUXURY VINYL PLANK & TILE FLOORING throughout. Mature trees, attractive landscaping and a quiet CUL-DE-SAC STREET add to the curb appeal, while a fully FENCED BACKYARD provides plenty of privacy. Inside, high ceilings and abundant natural light enhance the comfortable floor plan, featuring formal living and dining rooms at the front of the home and an open kitchen complete with STAINLESS STEEL APPLIANCES overlooking the family room and casual dining area. The SPLIT BEDROOM LAYOUT offers a private PRIMARY SUITE on one side of the home, complete with a spacious en-suite bath and WALK-IN CLOSET. Two additional bedrooms on the other side of the home share a full guest bath with convenient exterior access to the pool. Step outside to an expansive COVERED LANAI overlooking the PRIVATE SCREENED POOL with a deep end, creating the perfect setting for entertaining, relaxing or enjoying Florida's beautiful weather year-round. Additional highlights include a large laundry room and A/C in the garage for added comfort and flexibility. Silver Lake Forest is a sought-after, established community with a LOW HOA, zoned for “A” RATED Treadway Elementary and conveniently located near US-441, shopping, dining, entertainment and The Villages. Outdoor enthusiasts will appreciate being just minutes from Silver Lake, LAKE HARRIS and the Harris Chain of Lakes. With 3 bedrooms, 2 bathrooms, a generous lot and a fantastic poolside setting, this home checks all the boxes. Assumable VA loan available for qualified buyers – ask for details. Welcome home to Silver Lake Forest and WELCOME HOME!

32919 Indian Woods Drive, Leesburg
39 Hawaiian Way, Leesburg
$122,000
2 Beds ⋅ 2 Baths ⋅ O6449784 MLS
Welcome to 39 Hawaiian Way, located in the desirable Molokai Co-Op, 55+ community in Leesburg, Florida! This charming 2 bedroom, 2 full bathroom manufactured home offers an opportunity to enjoy affordable Florida Living in a community filled with amenities, activities and opportunities. Step inside and discover a comfortable and inviting floor plan designed for every day living. The Livingroom provides a welcoming space to relax or entertain, while the adjoining dining area offers a convenient place to gather for meals. The kitchen provides a functional space for preparing your favorite dishes, with easy access to the home's main living areas. The Primary Bedroom features its own bathroom, offering privacy and convenience, while the second bedroom provides additional space for overnight guests, hobbies, or a home office. With approximately 868 square feet of living space, this home offers a manageable layout with plenty of possibilities to make it your own. Outside, the covered carport provides convenient parking. Whether you are looking for a seasonal getaway or a full-time residence, this property offers the opportunity to embrace a relaxed Florida Lifestyle. ONE OF THE BIGGEST HIGHLIGHTS OF THIS PROPERTY IS THE AFFORDABLE CO-OP LIVING! This home is being sold with a Co-Op Share in the resident-owned Molokai 55+ community. For just $235.00 per month, residents enjoy an incredible value with the monthly cooperative fee INCLUDING WATER, SEWER, TRASH COLLECTION, BASIC CABLE, INTERNET, COMMUNITY POOL, AND ACCESS TO RECREATIONAL FACILITIES! The community features a beautiful clubhouse, swimming pool, shuffleboard courts, billiards room, library, and a variety of organized activities. Residents can enjoy social gatherings, card games, special events, clubs, and other opportunities to meet neighbors and enjoy an active lifestyle. With so many services and amenities included in one affordable monthly fee, Molokai Co-Op offers a wonderful opportunity for convenient Florida Living! LOCATION, LOCATION, LOCATION! Conveniently situated near shopping, restaurants, grocery stores, medical facilities, and major roadways, this home makes it easy to enjoy everything Lake County has to offer. Spend an afternoon exploring the charming downtown areas of Mount Dora, Tavares and Leesburg, where you will find local restaurants, boutique shopping, festivals, and year-round community events. Outdoor enthusiasts will appreciate the proximity to the beautiful Harris Chain of Lakes, known for boating, fishing, and waterfront recreation. Whether you are downsizing, searching for a winter retreat, or ready to enjoy the benefits of 55+ community living, 39 Hawaiian Way offers an opportunity to make the Florida lifestyle your own. Schedule your private showing today and discover everything Molokai Co-Op has to offer.

39 Hawaiian Way, Leesburg
35546 Calla Court, Leesburg
$699,900
4 Beds ⋅ 5 Baths ⋅ V4951773 MLS ⋅ 35546 BLDG.
Step Back in Time Without Giving Up Modern Comforts! This Waterfront Mid-Century Gem Is Seriously COOL! Love Mid-century architecture? You're going to fall for this one-of-a-kind 1957 waterfront property! Bursting with retro personality and vintage charm, it offers 201 feet of canal frontage just off Lake Eustis, access to the Harris Chain of Lakes, an oversized screened pool (10 feet deep!), and incredible entertaining spaces. The main home celebrates its mid-century roots with beautifully restored original Tennessee pink terrazzo floors and classic architectural details. The kitchen and main bathroom were updated in 2020, including an induction cooktop and convection oven, other improvements include replacement windows (2019), most of the electrical wiring updated, steel exterior entry doors (2019, excluding front and patio doors), added attic insulation, and new roofs in 2019–2020. Both buildings feature tankless water heaters. The second building offers over 1,200 square feet of possibilities! A renovated studio apartment (2020–2021) has enjoyed excellent short-term rental reviews and features a private patio and barbecue area. It's ideal for guests, extended family, or potential rental income. The adjoining lodge-style gathering space showcases a massive brick fireplace, original mid-century built-ins, vintage green linoleum floors, and kitchenette areas—perfect for parties, game nights, hobbies, and family gatherings. The oversized screened pool area is your own private retro resort! Highlights include a 10-foot-deep end, curved entry steps, original fiberglass slide, stainless-steel diving board dating to approximately 1963, and shallow-end spa jets. Fabulous decorative breeze block, a vintage pool bar, covered dining area with TV, generous entertaining space, and a large pool bathroom with shower complete this incredible outdoor retreat. Boating enthusiasts will love the 201 feet of canal frontage, two covered docks with electricity, and space for two additional boats. Enjoy cruising, fishing, and boating to waterfront restaurants along the beautiful Harris Chain of Lakes! Additional features include a large glass greenhouse, enclosed garage with coated floors, spacious workshop with potential vehicle or recreational storage, matching 10 x 10 storage shed, two driveways, and ample parking. A private well supplies household water, while canal water serves irrigation. Water treatment was updated in 2021 and 2026, and the septic systems mean no municipal water or sewer bills. A little retro, a little funky, and a whole lot of fabulous! With authentic 1950s-character, modern updates, separate guest quarters, exceptional entertaining spaces, and a prime waterfront location, this is more than a home—it's a rare opportunity to enjoy Old Florida charm and an unforgettable waterfront lifestyle!

35546 Calla Court, Leesburg
11347 Pine Ridge Road, Leesburg
$549,000
4 Beds ⋅ 3 Baths ⋅ G5118779 MLS
Virtually Staged. NO HOA CANAL- FRONT ranch home on a quiet street, with direct water access to the Harris Chain of Lakes right from your very own backyard! The canal leads to Lake Eustis and the rest of the chain of lakes within minutes. This 4-bedroom, 3-bath home offers 1,726 square feet on a 0.31-acre lot with 105 feet on the canal. Two of the 4 bedrooms share a Jack-and-Jill bath. Master bedroom is very spacious with a fully renovated bathroom in 2024 and doors leading to the lanai. The kitchen was fully renovated in 2023 with custom solid wood cabinetry and quartz countertops and newer appliances. The HVAC system and all duct work was replaced in 2023. The Windows, the water filtration system, and the drainfield were all replaced in 2020 and a full roof replacement in 2024. The newly renovated guest bath opens onto the 14-by-27 screened lanai overlooking the canal, here you will find a beautiful hot tub that does remain for your enjoyment! Along the canal you'll find the newly added 2024 covered entertainment area with a nautical rustic feel that has an insulated roof and ceiling fans to keep you cool while enjoying the outdoors!! Also located here is a fully functional bar with a refrigerator, the cowboy pool and boathouse that was added in 2024 with a pontoon lift giving the home its own boat storage and easy access to the chain of lakes. The seawall was also added in 2024. There is plenty parking and storage with an attached 2-car garage, a 12-by-55 custom carport attached to the home, a 12-by-24 shed/workshop with an attached carport, and a separate 10-by-10 storage shed all convey. Property is fully fenced as well. The location is convenient without feeling busy — Medical and shopping 5-10 minutes away. The Villages about 25 minutes and the Orlando area attractions under and hour away! Fantastic location, canal frontage with lake access, entertainment area on the canal! Boat house with lift! What more could you ask for?!!! Your paradise awaits! Call today!

11347 Pine Ridge Road, Leesburg
803 Dundee Circle Unit 803, Leesburg
$229,900
2 Beds ⋅ 2 Baths ⋅ G5118270 MLS ⋅ 803 BLDG.
Welcome to this beautifully upgraded 2-bedroom, 2-bath home with a dedicated office, located in Scottish Highlands, one of the premier Pringle communities in Lake County. Extensive remodeling includes a new roof, 2 new electrical panels, RELATIVELY new refrigerator, new washer and dryer, new gas heated hot water tank with circulation valve; luxury vinyl flooring throughout. Additional upgrades include new ceiling fans and light fixtures, carriage lights added to the garage, a new alarm system, and a convenient new exterior water tap at the front of the home, along with a surface-level water main shut-off valve; new toliets and new kitchen sink. The guest bath has a spa-like walk-in tub with jets along with a new sink, counter, toliet and ceramic floor tiles. On the exterior, a new concrete pad was installed for a stand-by gas generator, along with dedicated electrical power and an automatic transwer switch. The back porch has been upgraded to include steel footers and poly-resin, along with new flooring in this inviting outdoor living area. Step outside onto the back porch and enjoy tremendous views overlooking one of the community's small ponds—a peaceful setting for morning coffee, entertaining, or simply relaxing and enjoying the Florida lifestyle. Location is another highlight. The home is just a short distance from the clubhouse, where residents enjoy indoor and outdoor swimming pools, tennis and pickleball courts, and a wide variety of activities and social opportunities. With extensive recent improvements, beautiful water views, a versatile office, and an excellent location within Scottish Highlands, this home offers an exceptional opportunity to enjoy a move-in-ready Florida lifestyle in one of Lake County's sought-after Pringle communities.

803 Dundee Circle Unit 803, Leesburg
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