Leesburg Homes with Sidewalks Community Features

Leesburg Homes with Sidewalks Community Features

Welcome to Leesburg, Florida – a charming city nestled in the heart of Lake County, where Southern hospitality meets modern living. Known for its picturesque landscapes and friendly atmosphere, Leesburg offers a delightful blend of small-town charm and vibrant community life. With a rich history dating back to the 1800s, this city boasts a unique character that captivates both residents and visitors alike.

One of the standout features of Leesburg is its commitment to creating welcoming neighborhoods. Many homes in this area are part of communities designed with sidewalks, promoting a walkable lifestyle that encourages outdoor activity and connection among neighbors. Imagine taking leisurely strolls along tree-lined streets, where you can greet friendly faces and enjoy the beauty of your surroundings. These sidewalks not only enhance the aesthetic appeal of the neighborhoods but also provide safe pathways for families, joggers, and pet owners alike.

Leesburg is also home to a variety of amenities, including parks, recreational facilities, and local shops that cater to every need. The community hosts numerous events throughout the year, fostering a sense of belonging and camaraderie among residents. Whether you’re exploring the vibrant downtown area or enjoying a day at one of the nearby lakes, there’s always something to do in this lively city.

If you’re looking for a place that combines the warmth of community living with the convenience of modern amenities, Leesburg is the perfect choice. Discover your dream home in a neighborhood with sidewalks, where every day can be a new adventure!

Newest Leesburg Homes with Sidewalks Community Features

341 Ranchwood Drive, Leesburg
$319,000
3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph 01h SubDv. ⋅ 34748 Zip Code
Welcome home to 341 Ranchwood Drive, where privacy, flexibility, and the Pennbrooke Fairways lifestyle come together beautifully. Set against a peaceful, nature-filled backdrop, this thoughtfully maintained 3-bedroom, 2-bath home offers the kind of setting that makes it easy to forget how close you are to everything Central Florida has to offer. Step inside and you'll immediately appreciate a floor plan designed for comfortable Florida living. The main living spaces flow naturally together, while the split-bedroom design provides welcome separation between the primary suite and guest accommodations. An expansive 18' x 11' bonus area adds tremendous versatility—create a formal dining space, home office, reading room, hobby area, or simply additional room for entertaining. The primary suite offers a comfortable retreat with a generous walk-in closet and private bath featuring dual sinks and a walk-in shower. Two additional bedrooms provide plenty of space for visiting family and friends, an office, or whatever your next chapter requires. What makes this home particularly appealing is the combination of indoor comfort and outdoor living. A 9' x 17' screened lanai overlooks the home's private natural surroundings and creates an inviting spot to begin the morning with coffee or wind down at the end of the day. Just beyond it, the freshly refurbished open patio provides additional space for grilling, entertaining, or simply enjoying the Florida sunshine. The home has also seen substantial investment over the years, including a 2017 roof, 2017 windows and two sliding doors, added attic insulation in 2021, stainless-steel appliances in 2022, a new water heater and water softener in 2023, and a new HVAC system installed in April 2024 with a transferable warranty. Additional improvements include the lanai roof being re-shingled and the pavers resealed in 2024, along with painting of the front patio, garage, and porch in 2022. An oversized 2-car garage with dedicated golf cart access and a sliding screen adds even more functionality. Of course, buying in Pennbrooke Fairways is about more than the home. This gated 55+ community is built around an active Florida lifestyle, with golf, swimming pools, fitness facilities, pickleball, tennis, bocce ball, shuffleboard, cornhole, a restaurant, pro shop, Grand Hall, two recreation centers. The $265 monthly HOA fee includes cable, internet, lawn mowing and edging, plus boat and RV parking and storage. When you do decide to venture beyond the community, the location makes it easy. Lake Deaton Plaza—with Publix, Walgreens, dining and everyday conveniences—is just minutes away, while I-75, US-301 and The Villages are easily accessible. An evening of dining, shopping and live entertainment are just a short drive from home. 341 Ranchwood Drive isn't simply a place to live. It's an opportunity to have the privacy you want, the amenities you enjoy, and the freedom to make your next chapter in Florida exactly what you want it to be. WHO YOU WORK WITH TRULY MATTERS — LET US SHOW YOU WHY.

341 Ranchwood Drive, Leesburg
4719 Heritage Trail, Leesburg
$519,900
2 Beds ⋅ 2 Baths ⋅ Arlington Ridge SubDv. ⋅ 34748 Zip Code
BRING YOUR RV, BOAT OR CAR COLLECTION! Located on a private cul-de-sac in Arlington Ridge, this move-in-ready home offers 1,761 square feet of comfortable living, a LONG DRIVEWAY with plenty of room to pull in your RV, and a rare 50-by-16-foot RV garage with hookups, boat parking and a community pump-out station conveniently located just a block away. Major upgrades include a BRAND-NEW ROOF (2025) and whole-home Generac generator (2021), providing valuable peace of mind. Inside, you’ll find an inviting open layout with tile flooring, crown molding, plantation shutters and a gas fireplace. The beautiful kitchen features granite countertops, a center island, stainless steel appliances, pull-out storage and a breakfast nook. The spacious primary suite offers TWO walk-in closets and an ensuite bath with dual sinks, a garden tub and large walk-in shower. Outdoor living is just as impressive with a huge screened courtyard, retractable awning for shade and an expansive HALF-ACRE LOT offering plenty of backyard space to explore adding a pool. The location is fantastic, just minutes from UF Health Leesburg Hospital, with convenient access to Florida’s Turnpike and nearby P.E.A.R. Park offering hiking and biking trails, pickleball and a dog park. You’re also a short drive from The Villages town squares, shopping, dining and entertainment. Boaters will appreciate convenient access to nearby Lake Harris boat ramps and the incredible Harris Chain of Lakes for boating, fishing and waterfront dining. Arlington Ridge is a sought-after 55+ community offering a championship golf course, clubhouse, tavern, resort-style pools, fitness center, tennis, movie theater and an active Florida lifestyle. BEAUTIFUL UPGRADED HOME, RV GARAGE, A LARGE 1/2 ACRE LOT AND A GREAT CENTRAL FLORIDA LOCATION...THIS ONE HAS SO MUCH TO OFFER! Schedule your private tour today!

4719 Heritage Trail, Leesburg
27033 White Plains Way, Leesburg
$240,000
2 Beds ⋅ 2 Baths ⋅ Leesburg Arlington Ridge Ph 1-C SubDv. ⋅ 34748 Zip Code
QUICK MOVE-IN POSSIBLE! Built in 2020, Less than 1 block to the amenities, golf course, restaurant & pub, 2 bedroom, 2 bath with low maintenance concrete block & stucco villa with 1 1/2 car garage w/epoxy floor, 8 foot glass entry door for more natural light and lanai & birdcage with no homes behind it for added privacy. Enjoy the luxury feel of wood cabinetry, quartz countertops, waterproof LVP flooring, open kitchen perfect for entertaining, 4 seat bar-top, stainless kitchen appliances that stay, indoor laundry room with washer & dryer that stay, Low HOA of $303/month includes full lawn care, irrigation water & system, new roof when needed, exterior painting, high-speed internet, Wi-Fi, and over 200 cable channels. Community has On-site RV and boat parking available, . Safe & Secure gated community With hardly no yardwork to worry about, What will you do with all your free time? Arlington Ridge is more than a community it’s a way of living. Spend your mornings on the championship 18-hole golf course (no Membership Required. Pay only when you play as well as numerous amenities at no extra charge, Spend your afternoons at the heated pools or well-equipped fitness center with a pool view..., and your evenings with friends and neighbors at the on-site restaurant, tavern, or free movie theater. Enjoy tennis, pickleball, bocce, billiards, all just a 1 block walk or quick golf cart ride away. Take a peaceful stroll, walk the dog or bike ride along sidewalk lined streets. Conveniently located near shopping, dining, medical services, and a short drive to Orlando’s attractions and both coasts’ beaches, this home blends resort-style living with everyday practicality. Home includes gutters with lifetime leaf guard, power awning in bird cage, garage shelving, water softener & generator for the very rare times the power has been off. One of the most affordable communities to purchase homeowner's insurance in.

27033 White Plains Way, Leesburg
10427 Pleasant View Drive, Leesburg
$389,900
3 Beds ⋅ 2 Baths ⋅ Oakmont At Silver Lake Sub SubDv. ⋅ 34788 Zip Code
Virtually Staged. Welcome to your beautiful pool home in the heart of Leesburg! Situated on a quiet cul-de-sac, this inviting home offers the perfect combination of comfort, functionality, and Florida outdoor living. Inside, the open floor plan features sliding glass doors that showcase the beautiful pool views and create a seamless indoor-outdoor flow. The newly renovated kitchen offers modern finishes, Corian countertops, and a great view of the living room, making it ideal for entertaining and everyday living. A versatile office/flex space with French doors provides the perfect setting for a home office, playroom, or additional living space and could easily be used as a fourth bedroom. The split-bedroom floor plan offers privacy, with two bedrooms and a convenient pool bath located on one side of the home. The spacious primary suite features dual granite vanities, a walk-in shower, and a relaxing garden tub. Step outside and discover your own private backyard oasis. The sparkling pool includes a spa and a new pool heater, making it enjoyable year-round. The expansive pool deck and oversized, fully fenced backyard provide plenty of space for entertaining, pets, a trampoline, outdoor toys, or simply relaxing with family and friends. Mature trees add shade, privacy, and natural beauty, while the cul-de-sac location offers a peaceful setting. Conveniently located near shopping, dining, and access to the Chain of Lakes, this home truly checks all the boxes. With its renovated kitchen, flexible living spaces, private pool and spa, oversized fenced yard, mature landscaping, and numerous major updates, this is Florida living at its best!

10427 Pleasant View Drive, Leesburg
25078 Riverwalk Drive, Leesburg
$279,900
2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg SubDv. ⋅ 34748 Zip Code
Just bring your suitcase!!!!!! Beautiful 2 bedroom, 2 bathroom home with an additional bonus great for an office. Eat in kitchen has a pantry and a breakfast bar. The dining room is off of the living room. Home is fully furnished and ready to move in interior laundry, Florida room Stainless steel appliances, Gated community with 24 hour manned gate, 18 hole gulf course, 3 community pools, 3 clubhouses, Military Memorial, RV and boat storage, Restaurant, if you want an active or relaxing community this is the place to call home.

25078 Riverwalk Drive, Leesburg
512 Palo Verde Drive, Leesburg
$79,000
2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg SubDv. ⋅ 34748 Zip Code
Virtually Staged. Enjoy the best of Florida living in this charming 2-bedroom, 2-bath home located in the highly desirable 55+ community of Hawthorne at Leesburg! Offering resort-style amenities, a convenient Central Florida location, and a low-maintenance lifestyle, this home is an excellent opportunity for full-time residents or those seeking the perfect seasonal retreat. Ideally situated between The Villages and Orlando, you’ll enjoy easy access to shopping, restaurants, entertainment, medical facilities, and the Florida Turnpike. Inside, the home features a bright and functional kitchen with ample cabinet storage, an adjoining dining area, and a spacious living room that opens to an enclosed Florida Room. This additional living space is perfect for enjoying your morning coffee, relaxing with a good book, or entertaining friends and family year-round. The home offers two primary bedroom suites, each with its own full bathroom, providing comfort, privacy, and flexibility for visiting guests. Outside, the covered carport provides convenient sheltered parking, while the attached storage shed offers additional space for tools, seasonal décor, and other belongings. Hawthorne at Leesburg offers an exceptional resort-style lifestyle with an impressive array of amenities! Residents can enjoy a clubhouse, fitness center, sauna, tennis courts, pickleball, shuffleboard, bocce ball, card rooms, a softball field, and an 18-hole grass putting course. For boating and outdoor enthusiasts, the community also offers access to the Lake Harris Chain of Lakes, featuring boat slips and a private boat launch, along with boat and RV storage. Enjoy boating, fishing, water sports, and a variety of outdoor recreational activities, all adding to the appeal of this vibrant community. An active social calendar, clubs, and community events provide plenty of opportunities to meet neighbors and make lasting friendships. Whether you’re looking for a full-time Florida home, a seasonal escape from colder weather, or a place to enjoy an active and social retirement lifestyle, this home offers a wonderful opportunity to experience the Florida lifestyle you’ve been dreaming of!

512 Palo Verde Drive, Leesburg
3658 Caspian Street, Leesburg
$287,000
3 Beds ⋅ 2 Baths ⋅ Lake Denham Estates SubDv. ⋅ 34748 Zip Code
Virtually Staged. BEST-PRICED HOME IN LAKE DENHAM ESTATES! This 3-bedroom, 2-bath home offers 1,614 sq ft of comfortable living space, with solar panels to be PAID IN FULL by the seller at closing with acceptable offer, a fully fenced backyard, fresh interior paint, professionally cleaned carpets, and a 2-car garage. Eligible buyers may also qualify for USDA financing with 0% down.This 3-bedroom, 2-bath home offers 1,614 sq ft of comfortable living space along with PAID-OFF solar panels, a fully fenced backyard, fresh interior paint, professionally cleaned carpets, and a 2-car garage. Eligible buyers may also qualify for USDA financing with 0% down. Inside, you'll find a bright, open-concept layout connecting the living, dining, and kitchen areas, along with a split-bedroom floor plan that provides added privacy. The kitchen features a large center island with seating and prep space, stainless steel appliances, a gas range, generous cabinetry, and an oversized pantry. The spacious primary suite features a walk-in closet and private bath with a walk-in shower and generous vanity space. Two additional bedrooms and a full guest bath provide plenty of room for everyday living, guests, or a home office. Step outside to the covered lanai overlooking the fully fenced backyard, offering plenty of space for outdoor dining, entertaining, pets, or creating your own backyard retreat. Additional features include a hardwired security system that can remain with the home and transfer to the new owner with a separate monthly monitoring subscription, a tankless water heater, natural gas, and PAID-OFF solar panels. Lake Denham Estates offers a community pool, playground, park, and sidewalks, all while keeping you close to shopping, dining, entertainment, outdoor recreation, and Lake Harris. Downtown Leesburg is approximately 5 minutes away, with convenient access to Florida’s Turnpike for easy travel throughout Central Florida. Schedule your private showing today!

3658 Caspian Street, Leesburg
25419 Crestwater Drive Drive, Leesburg
$245,000
2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg, River Crest SubDv. ⋅ 34748 Zip Code
Welcome to the Plantation at Leesburg, a 55+ guard-gated community that enjoys a low HOA fee and many amenities. Upon entering the Foyer, you’ll appreciate the open floor plan which oversees the spacious Dining Room and Family Room. Four tall sliding glass doors allow for an abundance of natural light and lead to the screened 21’x23’ Lanai. The Kitchen is complete with granite countertops, ample cabinetry, an Eat-In Breakfast Area and a Laundry closet complete with washer & dryer. This 2 Bedroom, 2 Bath home with a Den offers a split-floor plan which allows privacy for you and visiting guests. HVAC 2022, ROOF 2017, new interior ceiling and wall paint 2026. This home is priced to sell. (Equal Opportunity Housing}. Easy To Show!

25419 Crestwater Drive Drive, Leesburg
5336 Tidewater Street, Leesburg
$325,000
2 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Riverside Village Lt SubDv. ⋅ 34748 Zip Code
Looking for a spectacular 2 bed + den home in the premier 55+ gated golf community of Plantation at Leesburg? Well, look no further! This exceptional property is striking from the moment you pull into the driveway, greeting you with updated landscaping, fresh exterior lighting, and a crisp, newly painted exterior. Open the front door and WOW—this home shows like an absolute model. The expansive layout features soaring ceilings and brand-new luxury vinyl plank flooring that flows seamlessly through the main living spaces. Every inch of the interior has been refreshed, including a STUNNING, brand-new custom Kitchen that belongs on the cover of a design magazine. This unique culinary space boasts: • Custom solid wood cabinetry in a sophisticated, trending sage green tone. • Striking pattern-tile backsplash that adds incredible character and designer flair. • Premium quartz countertops paired with a massive, commercial-grade stainless steel farmhouse sink and handsome modern hardware. • Brand-new 2026 appliances complete the ultimate chef's setup. The kitchen transitions beautifully into a sunlit breakfast nook accented by handsome rustic ceiling beams and stylish modern lighting fixtures. Slip away to the expansive primary suite, featuring a massive, completely updated bathroom that offers a true spa-like escape. Solidly built in 2004, the home also features an oversized garage. A spacious covered lanai—the perfect private oasis to enjoy your morning coffee or unwind in the beautiful Florida weather. With major components entirely updated, you can move in with total peace of mind: Roof (2023), A/C (2020), and a brand-new Garage Door Opener, Kitchen Appliances, and Disposal all new for 2026. Enjoy resort-style living at THE PLANTATION AT LEESBURG, A 55+ GATED COMMUNITY, with TWO GOLF COURSES, pools, tennis, pickleball, softball, clubs, and endless activities in one of Central Florida’s premier active adult communities. The life you have waited your whole life for is conveniently located near major hospitals, shopping, parks, and the airport. Don't miss this opportunity to own a move-in-ready home that offers comfort, quality updates, and exceptional outdoor living!

5336 Tidewater Street, 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
5418 Barnwell Court, Leesburg
$349,000
2 Beds ⋅ 3 Baths ⋅ Plantation At Leesburg Riverside Village SubDv. ⋅ 34748 Zip Code
Welcome to this beautifully maintained, one-owner home located in the sought-after 55+ community of The Plantation at Leesburg. Situated on a desirable corner lot, this spacious home offers a versatile floor plan with two primary bedrooms, each featuring its own en-suite bathroom, plus a separate den that could easily serve as a third bedroom, office, or hobby room. An additional half bath provides convenience for guests. The home features a separate living room, dining room, and family room, providing plenty of space for entertaining or relaxing. The family room overlooks the beautifully landscaped backyard, creating a peaceful setting to enjoy the Florida lifestyle. A charming breakfast nook offers the perfect spot for casual morning meals. Step outside to the large, screened lanai, an ideal place to enjoy your morning coffee, entertain friends, or unwind while taking in the beautiful surroundings. Additional features include Corian countertops, an inside utility room, and an abundance of well-maintained living space. Major updates include a new roof installed in 2024 and a top-of-the-line 4-ton, two-stage HVAC system installed in 2023, providing added comfort and efficiency. This home has been lovingly cared for by its original owner and is truly move-in ready. Furniture is also negotiable, offering buyers the opportunity for a convenient, furnished transition into their new Florida home. Located in The Plantation at Leesburg, residents enjoy a vibrant 55+ lifestyle with an array of amenities, activities, and opportunities to enjoy everything Central Florida has to offer.

5418 Barnwell Court, Leesburg
4711 Heritage Trail, Leesburg
$535,000
2 Beds ⋅ 2 Baths ⋅ Arlington Ridge SubDv. ⋅ 34748 Zip Code
Love to travel? Then you will want to see where the RV parks when you get home. This turnkey home is one of the few in Arlington Ridge with an RV garage, so your RV or motorcoach stays right at home. The RV garage measures 47' long x 15' wide with a 12' wide x 14' high door. Use it for an RV, boat, classic car, motorcycles, storage, or a workshop. It is in addition to a separate two-car garage, so there is no choosing between the things you love and the room to keep them. The community RV clean-out station is just down the street. Inside, the kitchen opens to the living room. Between the home and the RV garage sits a Tuscan-inspired courtyard with a gas stone fireplace, gas-lit wall sconces, a wrought-iron gate, and potted lemon and lime trees. It is a private spot for morning coffee or winding down after a day on the road. No rear neighbors adds privacy in the backyard, and HOA-approved pool renderings are available from the seller for anyone considering a future pool. Recent improvements include a 2023 roof and a 2026 A/C unit. The 18-hole championship golf course flows through the entire community. The low HOA for this home is $134.91 per month. It covers lawn mowing, edging, and blowing, premium cable TV, high-speed internet, and 24/7 paid security guards at the front gate. It also covers the resort-style amenities: fitness center, aerobics room, lap pool, and a large community pool with a beach area and a secluded hot tub. There is plenty to do. Catch a film in the movie theater. Head to Fairfax Hall for events, dancing, shows, and plays staged by the resident Little Theater Group. Join arts and crafts, social groups, and charities. Play tennis, pickleball, bocce, or softball on a community team. Walk or bike the trails. Enjoy great food at both the Grill and the Tavern. Arlington Ridge is a 55+ community that allows a set percentage of residents under 55. The Florida Turnpike, grocery stores, restaurants, medical offices, and hospitals are minutes away. Schedule your private tour and see how well this home fits the lifestyle you have been looking forward to.

4711 Heritage Trail, Leesburg
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