Leesburg / Haines Creek Homes with Pool Amenities

Leesburg / Haines Creek Homes with Pool Amenities

Welcome to Leesburg, Florida, a charming city nestled in the heart of Lake County, where the sun shines bright and the community spirit is warm. Known for its picturesque landscapes and vibrant local culture, Leesburg offers a unique blend of small-town charm and modern conveniences. The region is dotted with beautiful lakes, lush parks, and a variety of recreational activities, making it an ideal destination for families and outdoor enthusiasts alike.

One of the standout features of Leesburg is its diverse range of homes, many of which come with the sought-after pool amenities. Imagine stepping out of your back door into your own private oasis, where you can relax by the poolside, host summer barbecues, or enjoy a refreshing dip on a hot Florida day. Homes with pool amenities in Leesburg not only provide a luxurious lifestyle but also enhance your outdoor living experience, allowing you to soak up the sun and enjoy the beautiful weather year-round.

The community is rich in history and offers a plethora of dining, shopping, and entertainment options. Whether you’re exploring the historic downtown area, enjoying a day at the local farmer's market, or taking a scenic stroll along the waterfront, there’s always something to see and do. With its friendly atmosphere and welcoming neighborhoods, Leesburg is more than just a place to live—it's a place to thrive. Discover your dream home with pool amenities in this delightful region and experience the best of Florida living!

Newest Leesburg / Haines Creek Homes with Pool Amenities

803 Dundee Circle Unit 803, Leesburg
$229,900
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands SubDv. ⋅ 34788 Zip Code
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
37 Gordon Court, Leesburg
$189,900
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands Condo Ph B SubDv. ⋅ 34788 Zip Code
Virtually Staged. Welcome to easy Florida living in the desirable 55+ community of Scottish Highlands! Nestled beneath majestic oak trees on a quiet street, this well-maintained 2-bedroom, 2-bath home offers a comfortable split floor plan, peaceful wildlife and pond views. The home features vaulted ceilings that create an open, airy feel in the main living area, while the adjoining dining space provides a welcoming setting for everyday meals and entertaining. The kitchen features abundant cabinet and countertop space, a gas range, and a breakfast area, offering a practical layout with room to prepare meals and gather. The enclosed Florida room is a highlight of the home. Featuring vinyl windows, this versatile space is ideal for morning coffee, reading, hobbies, or simply unwinding. Enjoy views of the nearby pond and visiting wildlife from the Florida room and backyard—a peaceful backdrop to your daily routine. The primary suite includes a walk-in closet and private en-suite bathroom, while the guest bedroom and second bathroom provide comfortable accommodations for visitors or flexibility for your needs. An oversized one-car garage and ample storage complete the home's practical design. Lovingly maintained over the years, this home presents an excellent opportunity to settle in comfortably while updating and personalizing at your own pace. Scottish Highlands offers a variety of amenities and opportunities to stay active and connect with neighbors. Swim in the beautiful heated indoor 25-meter pool, equipped with an access lift, relax in the indoor hot tub, or enjoy the outdoor pool and sunbathing area overlooking a community pond. Tennis, pickleball, bocce, and shuffleboard courts provide options for recreation, with lighting at the shuffleboard and outdoor pool areas for evening enjoyment. The spacious recreation hall features a kitchen, stage, sound system, and extensive seating for community events. A separate clubhouse provides space for smaller gatherings, along with a movie and game library and kiln area. Residents can enjoy community breakfasts, dinners, dances, and other planned social activities. Additional amenities include a library, billiard room, and meeting rooms. RV and boat storage is available for an additional $18/25 monthly fee. Conveniently located near shopping, dining, and medical facilities, with historic downtown Leesburg and Mount Dora within easy reach, 37 Gordon Court combines everyday comfort with a welcoming golf cart friendly community lifestyle. Come discover the peaceful setting and possibilities waiting for you!

37 Gordon Court, Leesburg
11 Hawaiian Way, Leesburg
$69,900
2 Beds ⋅ 1 Baths ⋅ Molokai Co-Op SubDv. ⋅ 34788 Zip Code
This 2-bedroom, 1-bathroom home is perfectly sized for a new homeowner in the 55+ Molokai Co-Op community, where you own the land with no lot rent. The home features updated flooring throughout and new cabinetry in the kitchen. The inviting Florida Room is ideal for relaxing and enjoying the beautiful Florida surroundings. While you’re here, be sure to explore the community amenities, including the clubhouse, pool, and a variety of clubs you can join to make the most of life in the park.

11 Hawaiian Way, Leesburg
107 Diamond Head Drive, Leesburg
$103,000
2 Beds ⋅ 2 Baths ⋅ Molokai Co-Op SubDv. ⋅ 34788 Zip Code
Welcome to 107 Diamond Head Drive in the 55+ resident-owned Molokai community! This 2-bedroom, 2-bathroom home offers a pond view and an enclosed Florida room providing additional flexible living space. Enjoy the amenities of this active community, including a swimming pool, shuffleboard court, clubhouse, and much more. Conveniently located in Leesburg near shopping, dining, recreation, and everyday conveniences. Whether you're looking for a comfortable full-time residence or a place to enjoy the Florida lifestyle, this home offers the opportunity to become part of an established 55+ resident-owned community.

107 Diamond Head Drive, Leesburg
1113 Ben Hope Drive, Leesburg
$192,900
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands Condo Ph K SubDv. ⋅ 34788 Zip Code
Enjoy the Florida lifestyle in Scottish Highlands! This beautifully situated 2-bedroom, 2-bath home offers comfortable living, great outdoor spaces, and easy access to the many amenities this popular 55+ community has fo residents. A major highlight is the NEW ROOF, installed in 2025 and only one year old! That recent improvement provides valuable peace of mind for the new owner. The home also features a spacious living room/dining room combination plus a large separate great room—perfect for relaxing, entertaining, or creating a comfortable gathering space for family and friends. The home has a one-car garage and is surrounded by mature, nicely maintained landscaping with an irrigation system. Step outside and enjoy the Florida sunshine from the rear lanai, or use the separate patio area for grilling, outdoor dining, and entertaining. Scottish Highlands offers an outstanding selection of amenities, including both indoor and outdoor swimming pools, clubhouse/community center, tennis courts, pickleball and bocce courts. Onsite RV and boat parking is also available. Best of all, this home is conveniently located within the community and just a short walk from the amenities, making it easy to enjoy everything Scottish Highlands has to enjoy With a one-year-old roof, attractive outdoor spaces, spacious living areas, and an excellent selection of community amenities, this is a wonderful opportunity to enjoy the Scottish Highlands lifestyle. Come take a look!

1113 Ben Hope Drive, Leesburg
62 Aberdeen Circle, Leesburg
$225,000
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands Phase A& Aa Condo SubDv. ⋅ 34788 Zip Code
This beautifully reimagined 2-bedroom, 2-bathroom site-built home is located in desirable Scottish Highlands, a 55+ community. Thoughtfully renovated from top to bottom, this home offers modern finishes and a truly move-in-ready interior. Step inside to all-new windows, engineered hardwood flooring throughout the main living areas, ceramic tile in the bathrooms, and updated fixtures throughout. Both bathrooms have been beautifully renovated and feature gorgeous tiled showers and stylish finishes. The stunning new kitchen features shaker-style cabinetry, quartz countertops, stainless steel appliances, tile backsplash, deep stainless steel sink, and updated fixtures. A new sliding glass door leads to the finished lanai, providing additional flexible living space perfect for relaxing, entertaining, a home office, or hobby room. Additional features include an attached garage and detached storage shed, offering plenty of space for parking, tools, and storage. Located in Scottish Highlands, residents enjoy an active 55+ lifestyle with a heated indoor pool, outdoor pool, hot tub, tennis, pickleball, bocce, shuffleboard, clubhouse, recreation hall, library, billiards, and numerous community activities. RV and boat storage is also available for an additional fee, subject to availability. Conveniently located near shopping, dining, medical facilities, and the Harris Chain of Lakes. Beautifully renovated, thoughtfully designed, and ready for its new owner—schedule your private showing today!

62 Aberdeen Circle, Leesburg
21 Aberdeen Circle, Leesburg
$162,500
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
822 Dundee Circle, Leesburg
$215,000
2 Beds ⋅ 2 Baths ⋅ Scottish Highlands SubDv. ⋅ 34788 Zip Code
FRESH LOOK! If you took a peak at this gem before, it's time to take a second look in this popular 55+ community. We've completely transformed the interior by removing every last inch of carpet. The entire home now features brand new luxuary vinyl plank flooring-giving it a clean, modern and completely refreshed feel from the moment you step through the front door. NEW ROOF IN 2020, NEW ELECTRICAL PANEL IN 2023 along with fresh paint which makes this home move-in ready. You'll love the low maintenance yard--giving you back your weekends to enjoy everything this incredible active community offers. Friendly neighborhood known for top-notch amenities to include, indoor and outdoor community pools, shuffleboard, tennis, pickleball and community mailboxs, all in a golf cart friendly community. Best of all, you are just minutes away from medical facilities, fantastic shopping and a short drive to the HISTORIC downtown Mount Dora. Don't let this one slip away, schedule your appointment today.

822 Dundee Circle, Leesburg
1607 Selkirk Drive, Leesburg
$248,500
3 Beds ⋅ 2 Baths ⋅ Scottish Highlands Condo Ph P SubDv. ⋅ 34788 Zip Code
Virtually Staged. Beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, ideally situated in a desirable 55+ community that offers peaceful country-style living while keeping you close to everything. Mature landscaping creates attractive curb appeal, while the home’s clean, well-cared-for interior and comfortable layout make it easy to picture settling right in. Thoughtful updates include new flooring, a roof replaced in 2022, and HVAC installed in 2026. The kitchen is equipped with a gas range, and the home also offers gas heat—features that add everyday comfort and convenience. An irrigation well helps keep the landscaping looking its best, and the garage includes an extra refrigerator for additional storage and entertaining needs. Step outside to enjoy a private backyard with a new privacy fence extending across the rear of the property—an ideal setting for morning coffee, gardening, relaxing with a good book, or hosting friends and family. The 2-car garage provides ample space for vehicles, storage, and hobbies. Enjoy the convenience of nearby shopping, dining, entertainment, healthcare, and major roadways, all while coming home to a quiet, welcoming community with a relaxed setting. This lovely home offers a wonderful opportunity to enjoy the Florida lifestyle with comfort, convenience, and privacy.

1607 Selkirk Drive, Leesburg
219 Paradise S, Leesburg
$110,000
2 Beds ⋅ 2 Baths ⋅ Molokai Mhp Lt 02-Ha SubDv. ⋅ 34788 Zip Code
Welcome to this 2-bedroom, 2-bathroom home in Molokai, a 55+ resident-owned community. Located in the pet-friendly section of the park, this home offers an excellent opportunity to enjoy the Florida lifestyle with several major updates already completed. Energy Star windows were installed in 2021, and the roof was reroofed in 2023. The $235 monthly HOA fee includes water, sewer, cable, internet, pool access, and more, providing added value and convenience. Whether you're looking for a full-time residence or a seasonal getaway, this home is ready for its next owner. Schedule your showing today!

219 Paradise S, Leesburg
20 Hawaiian Way, Leesburg
$119,000
2 Beds ⋅ 2 Baths ⋅ Molokai Mhp Lt 02-Ha SubDv. ⋅ 34788 Zip Code
Welcome Home to 20 Hawaiian Way in Leesburg, Florida. (No lot rent) If you are looking for Move in Ready then you have found it! All of the big-ticket items have been taken care of and then some. This Home has received New AC, New Flooring, New Vapor Barrier, New Kitchen and New Appliances! The Home also has Newer Laminate Floors throughout, and the home is being offered Fully Furnished. Located in the No Pet section of Molokai but if you have a support animal with papers there are exceptions. The Home was built in 1980 and has 840 square feet with 2 Bedrooms and 2 Full bathrooms and a 1-car carport. The Washer and Dryer are located in the storage shed with Extra Storage Space. The Kitchen has lots of storage with New Cabinets and the perfect space with a dinette table. You have lots of Living space with a living room; features very light and bright with natural lighting from the Two Florida Rooms! The Primary Bedroom is spacious with an En-Suite Bathroom. The Home Features Two Florida Rooms. The First Florida Room is Enclosed and right off the Living Room. The Second Florida Room is Located with Slider doors from the Kitchen it is Screened in and overlooks the Carport. The home is Located in Molokai Co-op, a highly sought after and affordable 55+ Community in Leesburg, FL. Molokai offers lots of activities, a pool, a recreation center and your monthly fee includes cable, internet, water, trash and sewer. Not to forget the Location! You are close to Shopping, Restaurants and major highways. Also, you are not far from Downtown Mount Dora, Downtown Tavares and Downtown Leesburg and all the festivals and events that are offered! If boating and fishing are a favorite, you are only a short distance to a Public Boat Ramp for The Harris Chain of Lakes. Lake County FL offers something for everyone. Do not miss your chance to call this Home! Need financing? This home can be financed with a local lender, call for all the details and to schedule a Private Showing!

20 Hawaiian Way, Leesburg
9190 Harris Hawk Drive, Leesburg
$313,490
3 Beds ⋅ 2 Baths ⋅ Silver Lake Pointe SubDv. ⋅ 34788 Zip Code
Virtually Staged. The Portland is the perfect floorplan to take advantage of the Florida lifestyle. In this home guests are greeted by a covered entryway that leads into a spacious main level living area. No matter where you are in this space, the open floorplan is a great place for entertaining family and friends. The kitchen island, allows for natural movement through the main level, keeping the kitchen as the focal point of the home. Two spacious bedrooms share a hall bath on the main level, and the real showcase of this home is the primary suite which offers the utmost luxury and privacy. You have everything you need with dual vanities, a large walk-in closet, and standing shower. This home is an oasis for those looking for a new construction home, built for the way you live! *Photos are from a similar home.

9190 Harris Hawk Drive, Leesburg
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