Leesburg Homes with Maintenance Free Community Extras

Leesburg Homes with Maintenance Free Community Extras

Welcome to Leesburg, Florida – a hidden gem nestled in the heart of Lake County! Known for its charming small-town atmosphere, Leesburg is a vibrant community that offers a perfect blend of natural beauty and modern conveniences. With its picturesque lakes, lush parks, and a rich history, this city is an ideal place for families, retirees, and anyone looking to embrace the sunny Florida lifestyle.

One of the standout features of Leesburg is its array of homes within maintenance-free communities. Imagine living in a beautiful home where the worries of lawn care and exterior upkeep are taken care of for you! These maintenance-free communities are designed for those who wish to enjoy their time without the burden of chores. Here, you can spend your days exploring nearby lakes, indulging in local dining, or taking part in community events without the hassle of yard work.

In addition to the ease of maintenance-free living, residents of Leesburg enjoy access to a wealth of amenities. From sparkling swimming pools and fitness centers to walking trails and social clubs, these communities foster a sense of belonging and camaraderie among neighbors. Plus, with the stunning backdrop of Florida's natural landscapes, outdoor enthusiasts will find endless opportunities for fishing, boating, and hiking.

Whether you’re seeking a serene retirement haven or a family-friendly neighborhood, Leesburg’s maintenance-free communities provide the perfect setting to enjoy a relaxed lifestyle. Come discover the charm of Leesburg, where your dream home awaits!

Newest Leesburg Homes with Maintenance Free Community Extras

$325,000
3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Oak Tree Village SubDv. ⋅ 34748 Zip Code
Virtually Staged. “LOCATION LOCATION LOCATION NO CDD's! NO REAR OR FRONT NEIGHBORS!! BEYOND THE LOT, A CREEK! This BEST-LOVED HOME IS FAR from the noise of traffic. Through the canopy of oak trees rests this charming home. Situated behind hole 3 of the Otto Creek Par 72 course, the story of the construction of this home is recounted in a photo album as the original owners have lovingly built it from the ground up. From start to finish PRIDE OF OWNERSHIP MAKES THIS HOME SPECIAL from nail #1, throughout the years, to today. Note the expansive landscaping; gutters and private screened entrance. Even the sprinkler system has been overhauled complete with a new timer (2023/24). NEW ROOF IN 2025. NEW 50 GALLON WATER HEATER IN 2025! New/er appliances include: MICROWAVE in 2026; AC in 2020; Bosch dishwasher in 2021 (5 year warranty); LG refrigerator in 2025 (5 year warranty); Whirlpool stove in 2022 (5 year warranty); washer/dryer in 2022; garbage disposal in 2023. WDO BOND has been maintained with Florida Pest Control. When you enter, you will be confronted by warm ambiance graced with VAULTED CEILINGS of the large Great Room and Dining Combination which foreshadowed the OPEN PLAN that has come in vogue today. Beyond this space, venture into the spacious OFFICE/DEN which makes the LIVING SPACE SO MUCH BIGGER. Journey through the FRENCH DOOR onto the WOODEN DECKED GAZEBO – listen to the hush of the private rear garden. GAZE THROUGH THE GREEN EXPANSE, THIS LOT HAS ABOUT 1/4 ACRE OF REAR GARDEN!! Behind the lot is the Palatlakaha Creek, so the hush is going to be your daily peace! FEEL RIGHT AT HOME in the Kitchen and in the BREAKFAST NOOK, look through the bay window to see how your garden is growing and bask in the gleaming southwest sun. Notice the continuation of the VAULTED ceilings, the 18” tile floors, the beveled countertops and the solid wood cabinets. Continue your tour into the roomy PRIMARY SUITE which offers TWO WALK-IN CLOSETS. This private suite includes a RENOVATED ENSUITE complete with GROUT FREE SHOWER; BENCH SEAT; COMFORT HEIGHT TOILET which can be accessed through a WIDENED PRIVY DOOR; A DRESSING AREA (converted from a garden tub – don’t worry the plumbing is still there); and DIVIDED, RAISED VANITIES. You will enjoy the SPLIT PLAN privacy of MONTEGO model floor plan. Bedrooms 2 and 3 are very spacious. and bedroom 3 is larger and features a DOUBLE DOOR ENTRY (take a look at the floorplan included in the attachments). Bathroom 2 has a new vanity, comfort height toilet, and GROUT FREE tub/shower for easy breeeezzy maintenance. These owners were proud to build this home and had added $$$$$ of upgrades from the builder, and ever since this home has been well maintained in every area including the RECENTLY TREATED FLOORING IN THE OVERSIZED GARAGE and the fresh paint inside. Some Furniture could convey. Plantation is a 55+ community with 24-hour guard gate; two 18-hole golf courses, restaurant, 3 activity centers EACH with pools, fitness facilities, tennis and pickle courts, catch and release fishing, bocce and offers many events and clubs that will keep you very active. MAKE THIS BELOVED HOME YOUR BEST LOVED FOREVER HOME! GOLF CART with new batteries CONVEYS with accepted offer!

25845 Glen Eagle Dr, Leesburg
$400,000
3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph M Sub SubDv. ⋅ 34748 Zip Code
Resort-Style Amenities & On-Site Conveniences. Exceptional home you will not be disappointed in the 3/2 expanded Key Largo former model home on a premium Golf Course Lot on the 9th hole, overlooking a pond. Concrete block home with stucco exterior, open floor plan. Chef's in the family will be delighted with the oversized kitchen, with snack bar open to the breakfast nook with bay window and slider to the Family room. From there you can go outside on the caged patio area and enjoy your evenings pest free. The Den/Office area is wired for tv and 7.1 surround sound system. Expanded 2 car garage with privacy screen. Forget driving into town for basic errands or a night out. This unique, resident-owned community puts everything you need right at your fingertips:Dining & Pampering: Meet up with friends at the on-site restaurant, or book an appointment at the neighborhood hair and nail salon. Neighborhood Conveniences: Drop off mail or pick up packages directly at the neighborhood on-site post office.State-of-the-Art Fitness Center: Stay healthy and active with top-tier cardio and strength training equipment.Two Heated Swimming Pools: Enjoy year-round swimming, aquatic classes, or poolside relaxation.Endless Active-Adult Sports & RecreationYour toughest daily decision will be deciding which sport or activity to pick first. The extensive recreational facilities include:Championship Golf: Play across beautifully manicured fairways woven directly into the community layout.Dedicated Softball Fields: Join the local league or cheer on your neighbors from the stands.Racquet Sports: Fast-paced competitive play is always waiting at the tennis and pickleball courts.Traditional Lawn Games: Gather for social, outdoor fun at the shuffleboard courts, Bocce ball courts, Lawn Bowling green, or horseshoe pits.Unbeatable Location, When you do decide to venture out, you are perfectly positioned just minutes away from the endless town squares, nightly live entertainment, and dining options at The Villages Brownwood Paddock Square. Exceptional area shopping, diverse restaurants, and leading regional medical facilities are also right around the corner. Don’t miss this rare opportunity to own a piece of paradise in a community that truly has it all!

402 Grand Vista Trail, Leesburg
$388,790
3 Beds ⋅ 3 Baths ⋅ Leesburg Legacy Leesburg Unit 06 SubDv. ⋅ 34748 Zip Code
Welcome Home to Legacy of Leesburg! Looking for that perfect low-maintenance lifestyle in one of Leesburg's favorite 55+ communities? This 3-bedroom, 2.5-bath gem sits on a great corner lot and is ready for its next owner! Step inside and you'll immediately notice the vaulted and tray ceilings that give the home such an open, comfortable feel. The primary suite doesn't disappoint, it comes with its own private bath featuring a garden tub, a separate step-in shower, and a water closet for extra privacy. Love the look of wood but want easy upkeep? You'll appreciate the LVP flooring running through the main living areas, plus ceramic tile in all the right spots. The kitchen is a real highlight with gorgeous granite countertops, plenty of space to entertain, bake, or just spread out for a project. There's also a two-car garage and mature landscaping that gives the whole place a settled, established feel (no waiting years for trees to grow here!). Best of all, the HOA fee takes care of lawn mowing, edging, cable, and internet, so you can spend less time on chores and more time enjoying life. Of course, you can't beat what Legacy of Leesburg offers as a community — a pool, hot tub, billiards room, card room, RV/boat storage (at no additional charge) and plenty more ways to stay active and meet your neighbors. A couple of things to note: the home was updated in 2025, HVAC was replaced in 2025, plumbing was pressure tested and passed inspection, irrigation was given a full update, garage spring was replaced and roof (2012) was recently inspected and reported to be in great condition. This one's got it all — come see it for yourself!

27303 Gingerbread Place, Leesburg
$349,900
3 Beds ⋅ 2 Baths ⋅ Royal Highlands SubDv. ⋅ 34748 Zip Code
NEWLY RENOVATED IN ROYAL HIGHLANDS! This 3BR/2BA home in the gated 55+ active adult community is move-in ready with ceramic tile and luxury vinyl flooring throughout. The open floor plan features a beautifully updated kitchen with stone countertops, stainless steel appliances, and a large island with built-in gas cooktop. A built-in desk provides a convenient workspace adjacent to the kitchen, with a dinette nearby. The spacious primary suite offers a bath with walk-in shower and large garden tub. Enjoy the enclosed rear porch and paver patio overlooking lush lawns. Royal Highlands offers an 18-hole golf course, expansive recreation center with two pools, and four private lakes for fishing and canoeing, plus activities and amenities for an active lifestyle.

21506 Queen Anne Court, Leesburg
$275,500
2 Beds ⋅ 2 Baths ⋅ Legacy Leesburg SubDv. ⋅ 34748 Zip Code
Immaculate, 1401 sq ft, 2-bedroom, 2-bathroom custom Pringle Berkshire home in the premier 55-plus Legacy of Leesburg community. This floor plan has a true open-concept living space, with high ceilings and large windows to allow natural light into this space. In the kitchen, you have a large pantry and dedicated integrated dining space. Features an expansive bedroom setup complete with two separate walk-in closets and an en-suite bathroom boasting dual sinks, modern upgraded fixtures, and a walk-in shower. The back lanai has been fully upgraded to a glassed-in, air-conditioned living space, making it perfect for year-round use. Updates include: 2020 New Shingles, 2015 HVAC, 2024 water softener and driveway, and 2026 advanced lightning-rod safety protection infrastructure. The garage also has HVAC. This truly unique home is a must-see! Legacy is known for miles of scenic walking and biking trails through over 275 acres of conservation land, plus luxury amenities and on-site RV and boat storage. The neighborhood features a resort-style heated pool, a robust fitness center, and sports courts. Lawn care, cable, and internet are included in the amenity fees.

26958 Honeymoon Avenue, Leesburg
$89,900
2 Beds ⋅ 2 Baths ⋅ Leesburg Coachwood Colony 2nd Add SubDv. ⋅ 34748 Zip Code
Super location! No lot rent, HOA is not mandatory! You own the land! Two bedroom 2 bath home is priced to sell. Perfect for investors or buyers looking to invest some sweat equity. Newer roof and updated AC system. Spacious layout, attached oversized carport, and utility shed for storage. Conveniently located to downtown Leesburg, churches, restaurants, shopping, hospital and and doctors' offices. Come enjoy Bikefest, Mardi Gras chili cookoffs, and all the festivities that Leesburg offers.

2611 Carpenter Place, Leesburg
$239,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
A Masterfully Upgraded Florida Retreat. Welcome to a home that truly stands apart and thoughtfully upgraded to deliver exceptional comfort, craftsmanship, modern functionality, security, and peace of mind. This beautifully enhanced Florida retreat seamlessly blends contemporary sophistication with timeless warmth, creating a home that is as inviting as it is impressive. The expanded Florida room, completed in 2022, is a beautiful coastal-inspired space designed to warmly welcome guests and create an inviting atmosphere for gathering and relaxation. Thoughtful custom window treatments enhance the room’s character while allowing natural light to fill the space. Whether hosting friends, enjoying a quiet afternoon, or simply taking in the relaxed Florida ambiance, this versatile room adds a distinctive layer of charm and comfort to the home. At the heart of the home is a stunning, thoughtfully designed kitchen that makes the most of every inch. A smart, efficient open layout, with an expansive center island, abundant storage drawers, a walk-in pantry, sleek quartz countertops, high-end cabinetry, and luxurious finishes combine style and functionality, making this kitchen equally ideal for everyday living and entertaining. Throughout the interior, from the living room, dining room and bedrooms, luxurious vinyl flooring, upgraded windows, and custom interior doors create a refined and cohesive feel. The inviting bedrooms provide comfortable spaces to relax and unwind, while the beautifully updated bathrooms bring a spa-inspired experience with contemporary vanities and spacious walk-in showers accented by sleek sliding glass doors. The primary suite is a true standout, featuring an extra-large walk-in closet and a certified safe room, providing an added layer of security and protection during severe weather and other natural hazards. The extensive list of improvements provides both beauty and long-term peace of mind, including a new roof and vinyl siding in 2021, a new HVAC system in 2026, and completely updated electrical and plumbing systems. In 2026, the crawlspace was further enhanced with brand-new insulation, a vapor barrier, and ventilation fans to promote improved airflow and moisture management. Step outside and discover even more spaces designed for the Florida lifestyle. The beautiful front porch creates an inviting setting for morning coffee, evening relaxation, or entertaining friends and family. Just steps away, the heated and air-conditioned summer kitchen extends the living and entertaining space, making outdoor gatherings comfortable year-round. A versatile utility room and laundry room with ample storage add even more everyday convenience and functionality. This is more than a home, it’s a masterfully upgraded Florida retreat where beautiful design, coastal-inspired charm, smart functionality, thoughtful improvements, and genuine peace of mind come together. A home designed not only to impress, but to welcome, entertain, relax, and be cherished for years to come.

207 Hawthorne Boulevard, Leesburg
$99,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code
Come discover the charm of 106 Jasmine Trail! Tucked onto a generous corner lot, this well-cared-for 2-bedroom, 2-bath home offers a warm and inviting setting with a lovely neighborhood view from the Florida room. It’s the kind of space where you can slow down, enjoy a quiet morning, and feel at home. The sunlit, open living room features laminate flooring throughout, giving the home a fresh and easygoing feel. The kitchen is fully equipped, with tile flooring and a cheerful touch of natural light. Both bedrooms are spacious, offering comfortable retreats at the end of the day. The primary bath includes a walk-in shower with sliding glass doors, tile flooring, and a roomy countertop. The guest bath offers a tub with sliding glass doors, tile flooring, and generous counter space. Partially furnished and move-in ready, this home has been lovingly maintained and is ready for its next chapter. The membrane roof was installed in 2019, the HVAC system in 2020, and the water heater in 2014. With its bright interiors, roomy layout, corner-lot setting, and peaceful outlook, 106 Jasmine Trail is more than a house, t’s a place to make your own memories..............Hawthorne at Leesburg is an active, resident owned, 55+ cooperative, waterfront, gated community, with beautifully landscaped grounds, lakes with illuminated fountains and a relaxing and comfortable gazebo. The affordable monthly maintenance fee of $397 includes water, sewer, lawn mowing, private emergency services and storage space for recreational vehicles, boats, trailers and much more! The beautiful clubhouse is complete with a full-time program coordinator, more than 100 different activities and seating for 550. It has a hospitality lounge, card rooms, craft rooms, billiard room, fitness center, library, fine arts room and many more. There is excellent fishing, outdoor geo-thermally heated pool and two enclosed therapeutic pools. Hawthorne boasts a private marina monitored by an electronic security system with over 120 boat slips and access to the Harris Chain of Lakes and beyond.

106 Jasmine Trail, Leesburg
$269,000
2 Beds ⋅ 2 Baths ⋅ Pennbrooke Phase 1k, Unit Iii SubDv. ⋅ 34748 Zip Code
LOOKING FOR THE PERFECT FLORIDA RETIREMENT HOME? Welcome to 32901 Enchanted Oaks Lane, located in the desirable 55+ community of Pennbrooke Fairways in Leesburg! This well-maintained 2-bedroom, 2-bath home with a den/study and open Florida/sitting room offers an open, comfortable floor plan and is ready for its next owner to move right in and start enjoying the Florida lifestyle. Step inside and you will immediately notice the fresh, neutral interior, vaulted ceilings, abundant natural light and NO CARPET! The open living and dining areas provide plenty of room for entertaining family and friends, while the den/study offers additional flexible space for a home office, hobby room or guest space. The kitchen features an abundance of wood cabinetry, generous counter space, tiled backsplash, stainless steel appliances, breakfast bar and adjoining dining area surrounded by windows that bring in plenty of Florida sunshine. The spacious primary suite includes a private en-suite bath with barn doors and large walk-in closet, while the second bedroom and guest bath with no tub provide comfortable accommodations for visiting family and friends. One of the home's great features is the enclosed Florida room, providing additional space to relax, read a book, entertain or simply enjoy your morning coffee. Outside, the home's attractive landscaping, decorative edging, irrigation, gutters and spacious driveway contribute to its clean and welcoming curb appeal. ROOF 2021, A/C 2018, HOTWATER HEATER 2022 new ceiling fans throughout along with many other upgrades (see the attached list) add to the home's list of valuable features. And did we mention NO MORE MOWING? Lawn mowing is included through the HOA! Pennbrooke Fairways offers the active Florida lifestyle so many buyers are searching for, with golf, swimming pools, clubhouse, fitness and activity facilities, tennis, softball and numerous recreational and social activities. The community is conveniently located near The Villages, shopping, dining, medical facilities and entertainment, while its Central Florida location provides convenient access to Orlando-area attractions, airports and both Florida coasts. Whether you are looking for a full-time Florida residence or the perfect place to enjoy your retirement years, 32901 Enchanted Oaks Lane is ready to welcome you home. Schedule your private showing today! WHO YOU WORK WITH TRULY MATTERS — LET US SHOW YOU WHY.

32901 Enchanted Oaks Lane, Leesburg
$294,900
3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Oak Tree Village SubDv. ⋅ 34748 Zip Code
The expensive work is already done. Low-E double-pane windows (2023), HVAC (2021), water heater (2021), and a 2017 architectural shingle roof — the costly years are behind you. Move in, unpack, go play. Behind the 24-hour manned gate of The Plantation at Leesburg, this 3-bedroom, 2-bath ranch in Oak Tree Village lives larger than its 1,652 square feet. Vaulted ceilings and fresh neutral paint keep it bright, with laminate through the main living areas and ceramic tile in the wet spaces. The kitchen has been reworked — quartz counters, crisp white cabinetry with updated hardware, stainless appliances including a 2024 refrigerator — and opens to the dining area with built-in shelving, so no one is ever cooking alone. There is a separate formal living room and an electric fireplace for the handful of cool Florida evenings. The split plan puts the primary suite on its own side of the house: generous walk-in closet, private bath with garden tub, separate shower stall, dual sinks, and a freshly painted vanity. Two guest bedrooms and a second full bath sit opposite. Sliders open to the Florida room, where the windows crank open and the breeze does the rest — morning coffee, evening glass of wine. Also here: inside laundry room, water softener, 22x21 two-car garage, ceiling fan in every room, updated landscaping on a working irrigation system, a clear-sealed driveway, fresh paint on the front and garage doors, and a new storm door. At $180 a month, the HOA covers high-speed internet, lawn maintenance, private roads, and the 24-hour guard — plus two 18-hole golf courses, three clubhouses, three pools, sauna, fitness center, tennis, pickleball, racquetball, shuffleboard, and an on-site restaurant. Fenced RV and boat storage is available on site, which is genuinely hard to find. 2025 taxes: $1,872. Minutes from shopping, dining, and medical, with fast access to US-27 and public ramps to the famous Harris Chain of Lakes. The Plantation at Leesburg is a guard-gated 55+ community. Call today for a private tour.

25735 Glen Eagle Drive, Leesburg
$264,900
2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Greentree SubDv. ⋅ 34748 Zip Code
Welcome to 5350 Astor Street, a charming 2-bedroom, 2-bath home nestled on a desirable corner lot in the gated 55+ community of The Plantation at Leesburg. With 1,665 square feet of living space, this home offers a comfortable layout, inviting spaces, and plenty of natural light throughout. The AC was replaced in 2026 and comes with a 10-year transferable warranty, offering added peace of mind to the next owner. Step inside to the formal living and dining rooms, where bamboo flooring and abundant windows create a warm and welcoming first impression. The home features windows throughout, bringing in plenty of natural light. The kitchen is truly at the center of the home, featuring white appliances, ample cabinetry with convenient pull-outs, a breakfast nook, and a breakfast bar that opens to the family room. There’s a decorative backsplash in the kitchen and the open design makes it easy to stay connected with family and guests while preparing meals. The family room continues the bamboo flooring and opens through sliding glass doors to the screened-in lanai. With carpet flooring, the lanai offers a comfortable space to enjoy your morning coffee, unwind at the end of the day, or spend time with friends. Just beyond the lanai is a paver area overlooking the backyard, where a tall community-maintained hedge provides added privacy. The split-bedroom floor plan offers a comfortable sense of separation. The guest bedroom is located near the guest bath, which includes a tub/shower combination. The spacious primary bedroom features a large walk-in closet, while the primary bath offers a large shower, garden tub, double vanity, and comfort-height toilet. An interior laundry room is conveniently located near the center of the home for easy access. Beyond the home, enjoy everything The Plantation at Leesburg has to offer. This gated 55+ community provides an active Florida lifestyle with three activity centers, three pools, fitness facilities, tennis and pickleball courts, bocce, softball, fishing, and more. Golf lovers can enjoy two 18-hole golf courses, while the on-site restaurant and numerous clubs, groups, and activities provide plenty of opportunities to socialize, stay active, and enjoy the community. Whether you’re looking for a comfortable full-time residence or a place to enjoy your Florida lifestyle, 5350 Astor Street offers a wonderful combination of space, privacy, and community. Come take a look and imagine yourself calling The Plantation at Leesburg home.

5350 Astor Street, Leesburg
$279,000
3 Beds ⋅ 2 Baths ⋅ Highland Lakes SubDv. ⋅ 34748 Zip Code
Virtually Staged. WELCOME to 26744 Racquet Circle where your next chapter begins. Once through the welcoming screened entry way, you’ll be greeted by a spacious view of the living space with lots of natural light. The move-in ready, recently professionally painted 2,017 square foot home features luxury vinyl plank and tile flooring throughout, a 3-bedroom 2-bathroom split floor plan and an oversized 2-car garage with screen sliders. The bright and spacious kitchen with its stainless-steel package and gas range, Corian countertops, breakfast nook and bar with generous storage with pull-out cabinets and an abundance of countertops. The open concept of the kitchen overlooks the family room which is designed for both everyday living and entertainment. On the other side of the family room is a Florida room – a tranquil retreat with a wet bar to relax in or step outside to the adjoining screened patio which is perfect for outdoor living. The primary bedroom offers an ensuite bathroom with dual sinks, a jetted and relaxing soaker tub, a walk-in shower with a Rain showerhead, and a large walk-in closet. On the other side of the home, the spacious 2nd and 3rd bedrooms have oversized closets. This flexible floor plan is perfect for guests, hobbies or an office. Upgrades include a 2019 ROOF, a 2022 WATER HEATER, and recently installed REVERSE KITCHEN OSMOSIS and WATER SOFTNER SYSTEMS. The convenient indoor laundry room with a gas dryer adds to the home's convenience while the transferable termite bond brings peace of mind. The Carrier 2014 HVAC system has been maintained semi-annually. Highland Lakes is one of Lake County’s most established and rich amenity 55+ communities offering an impressive array of amenities for only $135- a month. Residents enjoy the sparkling indoor and outdoor pools along with a spacious clubhouse with a fitness center, game and meeting rooms, billiards and ping pong, a craft room with a kiln, an extensive library, a catering kitchen, an indoor arena with a stage for live entertainment and community events. Outdoor amenities include walking trails, fishing ponds, lighted tennis and pickleball courts, shuffleboard, bocce ball, horseshoe pits, a softball field with concession stand, a covered picnic pavilion with grills, a Craftsmen Club / Wood Working Shop (join for just $12 annually), an RV and boat storage (included in HOA), a golf driving range and catch and release fishing lakes. Enjoy the peaceful surroundings of Highland Lakes which are designed for an engaging lifestyle. Schedule a showing today!

26744 Racquet Circle, Leesburg
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