Leesburg / Haines Creek Homes with 55+

Leesburg / Haines Creek Homes with 55+

Welcome to the charming community of Leesburg, nestled in the heart of Lake County, Florida. Known for its picturesque landscapes and friendly atmosphere, Leesburg is an ideal place for those seeking a vibrant lifestyle, particularly for the 55+ community. With its inviting climate and abundant sunshine, this region is perfect for enjoying outdoor activities year-round.

Leesburg boasts a variety of amenities, including scenic parks, golf courses, and lakes that offer endless opportunities for fishing, boating, and leisurely strolls. The historic downtown area features quaint shops, delightful dining options, and a calendar filled with local events, ensuring that residents are never short of things to do. Whether you’re attending a farmers’ market or enjoying a community festival, there’s a sense of belonging in every corner of this lovely city.

For those aged 55 and over, Leesburg presents a wealth of housing options tailored to fit an active lifestyle. From well-appointed single-family homes to low-maintenance villas, the real estate market here caters to diverse preferences and needs. Many communities are designed specifically for retirees, featuring amenities such as clubhouses, fitness centers, and social activities that foster connections among neighbors.

In Leesburg, you’ll find not just a house, but a place to call home. Embrace the opportunity to enjoy a fulfilling life in this delightful region, where comfort meets community, and every day offers a chance to create lasting memories. Come explore the possibilities that await you in Leesburg, where your next chapter begins!

Newest Leesburg / Haines Creek Homes with 55+

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
1409 New Abbey Avenue, Leesburg
$219,900
2 Beds ⋅ 2 Baths ⋅ G5118503 MLS
Virtually Staged. SCOTTISH HIGHLANDS 55+ COMMUNITY – OVERSIZED LOT ** EXPANDED IMPERIAL MODEL WITH BONUS ROOM AND FLORIDA ROOM. **ALL NEW LUXURY VINYL PLANK FLOORING. ** BRAND NEW WATER HEATER. ** ROOF 2023. FRESHLY PAINTED. LONG DRIVEWAY LEADS YOU TO HOME WHICH FEATURES A COVERED SCREENED FRONT PORCH. AS YOU ENTER YOU WILL VIEW AN OPEN FLOORPLAN WITH CATHEDRAL CEILINGS AND AN ABUNDANCE OF NATURAL LIGHT. THE SPACIOUS KITCHEN OFFERS PLENTY OF CABINET AND COUNTERTOPSPACE AND HAS DINETTE AREA. TWO PANTRYS. SEPARATE DINING ROOM PROVIDES PERFECT SETTING FOR SPECIAL MEALS AND FAMILY GATHERINGS. BONUS ROOM CAN BE USED FOR OFFICE, HOBBY OR MUSIC AREA. ENJOY EVEN MORE LIVING SPACE IN THE FLORIDA ROOM WHICH IS A WONDERFUL SPOT TO RELAX AND VIEW OPEN BACKYARD. THE HOME FEATURES TWO NICE SIZE BEDROOMS WITH WALL CLOSETS. PRIMARY HAS EN-SUITE BATH WITH UPDATED VANITY AND DUAL SINKS, WALK IN SHOWER. GUEST BATHROOM WITH TUB/SHOWER COMBINATION. TWO LINEN CLOSETS IN HALLWAY. GARAGE HAS PULLDOWN STAIRS, SIDE ENTRY AND WASHER AND DRYER HOOKUP. FEES FOR SCOTTISH HIGHLANDS INCLUDE BASIC CABLE, INTERNET, PRIVATE SEWER AND ALL OF THE AMENITIES INCLUDING INDOOR OLYMPIC SIZE POOL,SPA, LIBRARY, OUTDOOR POOL, RECREATION BUILDINGS AND LOADS OF ACTIVITIES TO CHOOSE FROM. STORAGE FOR RV/BOAT AREA. VIEW TODAY AND MAKE THIS SCOTTISH HIGHLANDS HOME YOUR NEW ADDRESS.

1409 New Abbey Avenue, Leesburg
37 Gordon Court, Leesburg
$189,900
2 Beds ⋅ 2 Baths ⋅ G5118256 MLS
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 ⋅ G5118421 MLS
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 ⋅ G5117877 MLS
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
1032 Scotch Pine Court, Leesburg
$239,900
3 Beds ⋅ 2 Baths ⋅ G5118127 MLS
Virtually Staged. SCOTTISH HIGHLANDS 55+ COMMUNITY FEATURING INDOOR OLYMPIC POOL/SPA, OUTDOOR POOL, PICKELBALL AND MUCH MORE. THIS EXPANDED IMPERIAL MODEL HAS NEW ROOF IN 2023, NEW HVAC SYSTEM 2025, NEW WATER SOFTENER 2025. WELL FOR IRRIGATION! LOCATED ON A CUL-DE-SAC WITH OVERSIZED LOT, THIS 2/2 WITH DEN IS OPEN AND SPACIOUS. STEP INSIDE TO DISCOVER A LARGE LIVING ROOM WITH CATHEDRAL CEILINGS CREATING AN INVITING SPACE FOR ENTERTAINING AND RELAXING. FORMAL DINING ROOM WITH SLIDERS TO DEN/OFFICE OR HOBBY ROOM. LARGE KITCHEN WITH BREAKFAST BAR, TWO PANTRYS, TILED FLOORS AND LOADS OF CABINETS AND UPDATED COUTERTOPS. PRIMARY SUITE HAS TWO LARGE CLOSETS, POCKET DOOR FOR ACCESS IN TO THE BATH WITH JACUZZI TUB, WALK-IN SHOWER AND TILED FLOORS. GUEST BEDROOM IS LARGE 16X11. HALLWAY WITH 2 CLOSETS AND AN ADDITIONAL LINEN CLOSET. GUEST BATH HAS TILED FLOORS WITH WALK-IN SHOWER. REAR COVERED PORCH WITH GAS AVAILABLE FOR GRILL. GARAGE IS OVERSIZED 19X20 AND FEATURES PEGBOARD WALLS, WORKBENCH, LAUNDRY TUB, PULL DOWN STAIRS, SIDE ACCESS DOOR, SCREENED GARAGE DOOR. CENTRAL VACUUM, GUTTERS, UNDER TERMITE BOND, AWNINGS, 6 PANEL INTERIOR DOORS, LONG DRIVEWAY, FRONT COVERED PORCH. DON’T MISS THIE OPPORTUNITY TO MAKE THIS HOME YOURS!! SCOTTISH HIGHLANDS HAS FEES OF $220.00 WHICH COVERS YOUR AMENITIES, BASIC CABLE, INTERNET AND SEWER. GREAT CONVENIENT LOCATION CLOSE TO SHOPPING, RESTAURANTS AND MEDICAL AND WORSHIP FACILITIES.

1032 Scotch Pine Court, Leesburg
1113 Ben Hope Drive, Leesburg
$192,900
2 Beds ⋅ 2 Baths ⋅ G5118056 MLS
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
21 Aberdeen Circle, Leesburg
$162,500
2 Beds ⋅ 2 Baths ⋅ G5117934 MLS
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
2311 Bonnie View Court, Leesburg
$220,000
2 Beds ⋅ 2 Baths ⋅ G5117922 MLS
Virtually Staged. SCOTTISH HIGHLANDS STRETCHED IMPERIAL MODEL LOCATED ON A CUL-DE-SAC WITH .45 ACRE LOT. 2 CAR GARAGE WITH DEN/FAMILY ROOM AND ENCLOSED FLORIDA ROOM WITH VIEW OF LOVELY OAK TREES. WELL FOR IRRIGATION. UTILITY SHED FOR YOUR LAWN EQUIPMENT. NEW BREAKER BOX IN 2025. KITCHEN HAS UPDATED COUNTERTOPS WITH LOADS OF CABINETRY. STAINLESS STEEL REFRIGERATOR AND DISHWASHER. DISPOSAL. EAT IN DINETTE AREA WITH TILED FLOORS. SEPARATE DINING ROOM. LARGE LIVING ROOM WITH SOLAR LIGHT AND CATHEDRAL CEILINGS. DEN/FAMILY ROOM IN REAR WITH FRENCH DOORS AND AN ADDITIONAL ENCLOSED FLORIDA ROOM. PRIMARY BATH HAS 2 CLOSETS, POCKET DOOR TO BATH, WALK-IN SHOWER. GUEST BEDROOM IS LARGE WITH 2 CLOSETS. GUEST BATH HAS TILED FLOORS WITH TUB/SHOWER. TWO HALL LINEN CLOSETS. 15X7 FRONT SCREENED IN PORCH. GARAGE HAS PULL DOWN STAIRS AND IS 20 X 19, SIDE DOOR, PEGBOARD, LAUNDRY TUB. A GREAT COMMUNITY WITH INDOOR OLYMPIC SIZE POOL, SPA, RECREATION BUILDINGS, CRAFT ROOMS, POOL TABLE, LIBRARY, OUTDOOR POOL, TENNIS,PICKELBALL. FEES OF $220 COVER BASIC CABLE, INTERNET, AMENITIES AND PRIVATE SEWER. A LITTLE UPDATING AND YOU WILL HAVE A BEAUTIFUL NEW HOME

2311 Bonnie View Court, Leesburg
822 Dundee Circle, Leesburg
$215,000
2 Beds ⋅ 2 Baths ⋅ G5117500 MLS
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
65 Aberdeen Circle, Leesburg
$215,000
2 Beds ⋅ 2 Baths ⋅ G5117413 MLS
IMMACULATE AND MOVE IN READY – SCOTTISH HIGHLANDS BEAUTY!! THIS WELLINGTON SPLIT PLAN MODEL HAS TWO BEDROOMS AND TWO UPDATED BATHS. ROOF 2022. WATER HEATER 2017. OPEN FLOORPLAN WITH LARGE LIVING ROOM WITH VIEWS INTO KITCHEN AND DINING AREA. UPDATED VINYL PLANK FLOORING. KITCHEN HAS BEEN UPDATED WITH CABINETRY, STAINLESS STEEL APPLIANCES, DISPOSAL, M/W, GAS STOVE ON ISLAND, BREAKFAST BAR. PRIMARY BEDROOM AREA HAS EN-SUITE BATH WITH WALK-SHOWER AND NEWER VANITY AND 10 X 5 WALK-IN CLOSET, TILED FLOORS. NO CARPET IN HOME. GUEST BATHROOM HAS BEEN REMODELED WITH VANITY, SINK, TOILET, TUB/SHOWER COMBINATION. FLORIDA ROOM HAS LARGE WINDOWS WHICH ALLOWS FOR GREAT VIEWS AND SUNLIGHT. (no direct rear neighbors) PAVER PATIO GREAT FOR ENTERTAINING, GRILLING AND JUST CHILLIN! GARAGE IS OVERSIZED 29 X 12 WITH WASHER AND DRYER AND REAR ENTRY, NEW GARAGE DOOR OPENER, ATTIC ACCESS. NEWER FRONT AND BACK STORM DOORS. HOME HAS 6 TV OUTLETS. UPDATED LIGHTING AND CEILING FANS. GUTTERS. JUST PRESSURE WASHED. SCOTTISH HIGHLANDS FEES INCLUDE BASIC CABLE, INTERNET, PRIVATE COMMUNITY SEWER AND RECREATION FACILITIES. INDOOR OLYPMIC SIZE POOL, SPA, OUTDOOR POOL, TENNIS, PICKELBALL AND LOADS OF ACTIVITIES TO CHOOSE FROM. DON’T MISS THIS OPPORTUNITY TO MAKE THIS SPECIAL PROPERTY YOUR NEW HOME!!

65 Aberdeen Circle, Leesburg
1607 Selkirk Drive, Leesburg
$245,000
3 Beds ⋅ 2 Baths ⋅ G5117038 MLS
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
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