Leesburg Homes with Sidewalks Community Features

Leesburg Homes with Sidewalks Community Features

Welcome to Leesburg, Florida – a hidden gem nestled in the heart of Lake County, where charming small-town vibes meet modern conveniences. Known for its picturesque landscapes and vibrant community, Leesburg offers a unique blend of history and progress. With its quaint downtown area, rich cultural heritage, and stunning lakes, this city is perfect for those seeking a serene lifestyle amidst nature's beauty.

One of the standout features of Leesburg is its commitment to creating a welcoming environment for families and individuals alike. The city boasts a variety of homes with sidewalks, making it easy to enjoy leisurely strolls through the neighborhood or take an evening bike ride. These pedestrian-friendly communities encourage a sense of connection among residents, fostering friendships and a tight-knit atmosphere.

In addition to its beautiful homes, Leesburg offers an array of amenities to enhance your living experience. Residents can enjoy parks, recreational facilities, and local events that celebrate the community's spirit. The nearby lakes provide ample opportunities for fishing, boating, and enjoying the great outdoors, while the local shops and restaurants offer delightful options for dining and entertainment.

Whether you're a first-time homebuyer, a growing family, or looking to retire in a peaceful setting, Leesburg has something for everyone. Discover the charm of this vibrant city, where homes with sidewalks invite you to embrace an active lifestyle and connect with your neighbors. Come and experience the warmth of Leesburg, where community and comfort go hand in hand!

Newest Leesburg Homes with Sidewalks Community Features

3 Beds ⋅ 2 Baths ⋅ Highland Lakes Ph 2-C SubDv. ⋅ 34748 Zip Code

Meticulously maintained single family BLOCK & STUCCO home is ready for new owners! Landscaped CORNER LOT | PAVER DRIVE AND WALK | 3-bedrooms | 2 bath | DOUBLE PANE WINDOWS | GENERAC GENERATOR | Luxury Vinyl Plank flooring throughout | Living and dining room combination | vaulted ceiling | eat-in kitchen featuring Cambria QUARTZ countertop, Bay Window, REFACED CABINETS and all appliances convey | INTERIOR LAUNDRY ROOM | FOUR-SEASON SUNROOM for year round comfort and enjoyment | KNOCK-DOWN ceiling texture | Primary Retreat boasts His & Her walk-in closets, UPDATED ensuite bath, SEAMLESS GLASS shower enclosure, new vanity with DUAL SINKS and QUARTZ countertop, PLANTATION SHUTTERS | split bedroom layout with two additional bedrooms share the guest bath with tub-shower combination. OVER-SIZED garage features 528sf | ROOF 2022 | HVAC 2020 | Water Heater 2017 | UPDATED electrical panel Highland Lakes is a gated 55+ community situated in Central Florida just south of Leesburg & offers residents the following amenities: Recreational Clubhouse with two swimming pools; indoor (heated) & outdoor, a softball field complete with concession stand, an indoor arena with a stage for comm. events, complete kitchen, billiard/ping pong rm., 4 tennis courts (2 courts are lighted), 1 indoor tennis court, 8 lighted shuffle board courts, bocce ball courts, 2 outdoor and 4 indoor pickleball courts, 7 horseshoe pits, covered picnic pavilion with picnic tables & grills to barbeque, library, meeting/card room, exercise room/fitness, craft room, golf driving range, RV/boat storage (included in HOA) & has 260 spaces on a secured lot (fenced & lockable), a Craftsmen building/woodworking shop (homeowners can join the club for only $12 annually and use any/all tools available), there's also a Nature Trail within the community & seven lakes scattered throughout Highland Lakes; 4 are used by residents for catch & release fishing! Don't wait............. call now to schedule your private tour!

26920 Racquet Circle, Leesburg

3 Beds ⋅ 2 Baths ⋅ Legacy Of Leesburg Unit 02 Lt 163 SubDv. ⋅ 34748 Zip Code

Virtually Staged. Welcome to the gated and secure 55+ community of Legacy of Leesburg! This beautiful, established neighborhood offers a peaceful Central Florida setting with numerous lakes, nature trails, mature trees, conservation areas, and larger homesites. This move-in-ready Colchester model has been freshly painted inside and out and features brand-new appliances. The desirable split-bedroom floor plan provides privacy and functionality, while the open-concept design showcases attractive laminate flooring, crown molding, and a spacious kitchen that flows seamlessly into the family room. A separate dinette area provides additional space for casual dining. Legacy of Leesburg offers an impressive array of amenities with low monthly fees that include landscaping, cable, and Wi-Fi. Residents enjoy an active lifestyle with a resort-style pool and hot tub, fitness center, bocce ball, pickleball, billiards, shuffleboard, library, craft room, card room, tennis, and a newly renovated social hall. There is also a baseball field, walking trails, mature trees, and numerous peaceful areas for nature and bird watching. Legacy is a mature, well-established community with its own conservation areas and convenient access to Central Florida's many lakes and rivers. The community's builders have received numerous awards, adding to the appeal and quality of this neighborhood. The location is convenient to shopping, dining, and major roadways, including the Florida Turnpike. Disney attractions and the Orlando International Airport are also within an easy drive. Just outside the community, you'll find Rodello's Italian Restaurant and a nearby dog park. Publix Super Market at Lake Harris is conveniently located for everyday grocery shopping, and ALDI is coming soon to the area. Located in the heart of Leesburg, this home offers the perfect combination of comfort, convenience, amenities, and an active 55+ lifestyle. If you're looking for a move-in-ready home in a beautiful, safe, and secure community, this property is an excellent opportunity!

5325 Fantasy Way, Leesburg

3 Beds ⋅ 2 Baths ⋅ Leesburg Legacy Leesburg Unit 06 SubDv. ⋅ 34748 Zip Code

THIS POPULAR CARLISLE MODEL HOME HAS 1765 SQUARE FEET WITH 3 BEDROOMS 2 BATHROOMS. THE KITCHEN HAS UPGRADED CABINETS, CORIAN COUNTERS, STAINLESS STEEL APPLIANCES. JUST OFF THE KITCHEN IS THE BREAKFAST NOOK WHERE YOU CAN ENJOY THAT FIRST CUP OF COFFEE. 2 GUEST ROOMS AND A GUEST BATH THAT HAS BEEN TRANSFORMED INTO A WALK IN SHOWER. CLOSETS BY DESIGN HAS UNIQUELY CONFIGURED ALL THE CLOSETS TO MAXIMIZE SPACE AND STORAGE. PLANTATION SHUTTERS, DOUBLE PANE WINDOWS. THE EXTERIOR OF THE HOME WAS PAINTED 2026. THE HOME WAS CONVERTED TO TOTAL ELECTRIC IN 2024 WHICH INCLUDED THE WATER HEATER AND HVAC SYSTEM. ROOF WAS REPLACED IN 2019. THE AIR CONDITIONED LANAI WAS CONVERTED TO A FORMAL DINING AND OUTDOOR SPACE WAS ADDED. THIS IS A PERFECT WINTER HOME IN A PERFECT COMMUNITY, LEGACY OF LEESBURG IS A NATURE THEMED COMMUNITY OFFERING WALKING TRAILS, MILES OF CONSERVATION. MILLION DOLLAR RENOVATION IN 2025, A RESORT STYLE POOL, PICKLEBALL, TENNIS, BOCCE, SOFTBALL FIELD, ON SITE RV AND BOAT STORAGE, AND A ACTIVITIES DIRECTOR THAT WILL KEEP YOU BUSY ALL DAY. CABLE AND INTERNET ARE INCLUDED IN THE AFFORDABLE HOA AS WELL AS GRASS CUTTING AND TRIMMING. SELL ALL YOUR LAWN EQUIPMENT, AND COME AND RELAX, YOU HAVE EARNED IT. COME SEE WHY SO MANY CALL LEGACY HOME.

27336 Pine Straw Road, Leesburg

3 Beds ⋅ 3 Baths ⋅ Royal Highlands Ph 01b SubDv. ⋅ 34748 Zip Code

Virtually Staged. Desired Duke Model with 3 bedrooms, 3 baths, 2,369 sq. ft. under air, and an enclosed rear lanai overlooking peaceful pond views. This sought-after floor plan is known for its large private courtyard and separate casita ensuite—ideal for guests, multigenerational living, or anyone who appreciates a private retreat. The casita features a Murphy bed that conveys with the sale, a three-piece bath, walk-in closet, and its own temperature control. Situated on an oversized lot, this home offers a 2026 roof, irrigation, a whole-house generator, and an oversized 22 x 27 garage. Inside, the kitchen features granite counters, wood cabinetry, stainless steel appliances, and a dinette with charming courtyard views and lush garden scenery. Additional features include abundant closet space, solar skylights, sliders, engineered wood floors, high ceilings, and generous room sizes throughout. The primary suite offers a jetted tub and step-in shower, while the flexible bonus space is perfect for an office, music room, or reading retreat. Designed for entertaining, the Duke delivers spacious living areas, privacy, and spectacular pond views from nearly every room. Priced to find its buyer quickly—do not delay! Come tour this special home in Royal Highlands, a 55+ active, gated golf community offering two pools, a fitness center, Great Hall with entertainment stage and dance floor, courts, clubs, and more. Conveniently located near Florida’s Turnpike, MCO, attractions, historic districts, shopping, restaurants, medical facilities, and The Village Squares.

21815 Tartan Street, Leesburg

4 Beds ⋅ 2 Baths ⋅ Ashton Woods SubDv. ⋅ 34748 Zip Code

Spacious, stylish and filled with beautiful architectural details! This spacious 4-bedroom, 2-bath home offers approximately 2,420 square feet of living space and is situated on a desirable corner lot with a wonderfully private backyard. Step inside to an impressive open and inviting floor plan featuring beautiful wood flooring, high ceilings, crown molding, architectural details, tray and coffered ceilings, and abundant natural light. The home offers flexible living spaces perfect for entertaining, working from home, or simply spreading out and enjoying everyday living. The kitchen opens to the main living areas and features granite countertops, rich wood cabinetry, stainless steel appliances, a breakfast bar, and adjoining dining space. The spacious primary suite offers an impressive tray ceiling and plenty of room to create your own private retreat. One of the home's standout features is the large screened-in rear porch, perfect for relaxing, entertaining, enjoying morning coffee, or unwinding at the end of the day while overlooking the very private backyard. Additional highlights include a 2-car garage, inside laundry, attractive landscaping, brick-paver accents, and a spacious .27-acre lot. Location is another wonderful advantage! Enjoy convenient access to Downtown Leesburg, Tavares and charming Downtown Mount Dora, with their restaurants, shopping, waterfront activities, festivals and year-round events. The home is also within easy reach of The Villages and major Central Florida roadways including US-441, US-27 and SR-44, providing convenient connections toward Florida's Turnpike and the greater Orlando area. Spacious, distinctive, private and centrally located—this beautiful home is ready for its next owner!

301 Ashton Woods Lane, Leesburg

2 Beds ⋅ 3 Baths ⋅ Arlington Ridge SubDv. ⋅ 34748 Zip Code

THIS is what Florida retirement should look like! Welcome to 4419 Bent Creek Lane, a custom-built 2019 home offering over 2,300 SQFT on a premium cul-de-sac lot within the guard-gated, 55+ golf community of Arlington Ridge. Thoughtfully designed with ADA accessibility at the forefront, this home combines comfort, functionality, and modern Florida living. The open, split-bedroom floor plan features TWO PRIVATE PRIMARY-style suites with en suite baths, plus a spacious 15' x 14' den/office that can easily serve as a THIRD BEDROOM. Accessibility features are incorporated throughout the home, complemented by ADA compliant handrails, curbless walk-in showers, and heated bathroom floors in the main primary suite for an added touch of everyday luxury. This home also features solar tubes for additional natural lighting, a full-home smart system, granite countertops throughout, soft-close cabinetry, pull-out kitchen shelving, and a generously sized laundry room with additional cabinetry and utility sink. Out back, your private screened retreat is ready for year-round enjoyment with a heated saltwater lap pool featuring an ADA-certified pool lift, PLUS an 8-person Jacuzzi that conveys with the home. Additional upgrades include a Generac whole-home generator, two auxiliary generators, whole-house water treatment, Bluetooth water-leak detection, and a pavered driveway and entry. Beyond the home, Arlington Ridge delivers the resort lifestyle with a Gary Koch-designed golf course, community pools, pickleball, tennis and bocce courts, fitness center, sauna, movie theater, recreation facilities, and an on-site café, restaurant and pub. The community is golf cart friendly, and the HOA includes lawn mowing, cable TV, and internet. Comfort. Accessibility. Amenities. Florida living. 4419 Bent Creek Lane brings them all together in one incredibly unique home. Schedule your private showing today!

4419 Bent Creek Lane, Leesburg

2 Beds ⋅ 2 Baths ⋅ Hawthorne At Leesburg A Coop SubDv. ⋅ 34748 Zip Code

Virtually Staged. FURNISHED 2-BEDROOM HOME IN HAWTHORNE AT LEESBURG! Looking for a spacious Florida home in an active, award-winning 55+ community? This 1,350 sq. ft., 2-bedroom, 2-bath manufactured home in Hawthorne at Leesburg is being sold furnished and has several important improvements already completed! HOME FEATURES & UPDATES New windows, roof-over, and new exterior vinyl siding in 2011. New water heater in 2024. Newer sprinkler system. Shrubs were removed, and landscape rock was installed for easier maintenance. Laminate flooring in the kitchen, living room, and dining room. Carpet in bedrooms, vinyl flooring in the bathroom. Being offered furnished, the owner will provide an inventory list. This home offers plenty of space for comfortable year-round or seasonal Florida living. With many of the exterior improvements already completed and furnishings included, you can move in and start making it your own. Hawthorne at Leesburg is a private, gated 55+ community offering an exceptional variety of amenities, activities, and services in a relaxed setting. Whether you prefer an active social calendar, recreation with friends, or a quiet afternoon by the pool, Hawthorne offers something for everyone. Community amenities include: Outdoor geothermal-heated swimming pool and two enclosed therapeutic pools Fitness room, saunas, library, clubhouse with Wi-Fi, card rooms, and billiard room Tennis, pickleball, bocce, croquet, and 24 lighted tournament-class shuffleboard courts Softball field, putting area, and 18-hole pitch & putt course Two dragon boats for recreational and competitive use Garden plots and RV, boat, and trailer storage Courtesy bus service with door-to-door transportation for scheduled shopping and errands Annual concert series and a wide variety of clubs, games, and social activities Hawthorne also offers additional amenities for a separate fee, including a 120+ slip marina with an on-site boat launch, a fully equipped 1,500+ sq. ft. woodcrafters’ shop, and an on-site laundromat. Contact the HOA for current availability and fees. A standout feature of Hawthorne is its private, community-dedicated emergency response services. State-certified firefighter/EMTs are on duty 24/7, with emergency response vehicles located within the community. Homes are equipped with emergency alarm buttons, and remote necklace alarms are available for an additional fee. The community also features a staffed gatehouse, controlled-access entrances, and routine community patrols. Hawthorne at Leesburg combines recreation, convenience, security, and an active lifestyle, all within one established 55+ community.

104 Caladium Street, Leesburg

4 Beds ⋅ 3 Baths ⋅ Liberty Preserve SubDv. ⋅ 34788 Zip Code

Auction Property. No Rear Neighbors! Discover the Providence by Lennar—a beautifully appointed and move-in-ready two-story home offering 4 bedrooms, 2-and-a-half baths, all in a quiet serene setting but so close to it all! The main level welcomes you with a spacious open-concept design that flows effortlessly from room to room. At the heart of the home, the espresso-finished kitchen, featuring stainless steel appliances, solid-surface countertops, wood-look plank tile flooring, and a center island overlooking the expansive dining and family rooms—an ideal layout for everyday living and entertaining. A versatile flex room provides additional space for a home office, library, hobby room, and even storage. Upstairs, all four bedrooms surround a comfortable loft that’s perfect for movie nights, games, reading, or relaxing. The generous owner’s suite offers a roomy walk-in closet and a private bathroom with dual sinks, along with a lovely view of the lake. A centrally located upstairs laundry room adds convenience right where it’s needed most. Lennar’s 'Everything’s Included' features elevate the home with stylish finishes throughout, including oversized tile flooring in the wet areas. Liberty Preserve offers convenient access to outdoor recreation, local gardens, parks, shopping, dining, and everyday essentials. Ideally situated near Highways 44 and 441, the community is also convenient to Venetian Gardens, UF Health Leesburg, and Leesburg International Airport. With its spacious layout, thoughtful features, and lovely homesite, this home is a standout opportunity. Schedule your private showing today!

33622 Sky Blossom Circle, Leesburg

3 Beds ⋅ 2 Baths ⋅ Windsong At Leesburg SubDv. ⋅ 34748 Zip Code

Welcome to 5516 Windsong Oak Drive, an exceptionally upgraded, light & bright 3-bedroom, 2-bath home featuring a huge 3-car garage, a 0.28-acre homesite, & a cozy covered back porch, perfect for morning coffee or evening relaxation. Built in 2020 by Hanover Family Builders, this home offers a rare combination of premium finishes, thoughtful upgrades, & long-term affordability. All appliances, including the washer and dryer, plus all window treatments, are included. The community also features a pool & playground just moments from your front door. Step inside and you'll immediately appreciate the spacious feel created by the 9-foot, 3-inch ceilings, abundant natural light, upgraded porcelain tile flooring throughout the main living areas & bathrooms, designer matte black hardware and fixtures, ceiling fans, stylish lighting with dimmers, and upgraded door hardware. This is far from a cookie-cutter home—every finish has been thoughtfully enhanced. The beautifully appointed kitchen serves as the heart of the home, featuring upgraded cherry cabinetry with 42-inch upper cabinets, elegant angled crown molding, convenient triple-drawer base cabinets, quartz countertops, a Kohler Vault K-15160-CP stainless steel double-basin apron-front sink, garbage disposal, three designer pendant lights, and a microwave vented directly to the exterior. A spacious center island with a breakfast bar overlooks the family room, creating an ideal layout for entertaining. Just beyond, the covered back porch extends your living space outdoors, making gatherings with family and friends effortless. The primary suite is a true retreat, enhanced with two additional windows that fill the room with natural light. The spa-inspired bathroom features a frameless glass shower, an upgraded Kohler electric push-button rainfall shower system, a private water closet, a matching triple-drawer vanity cabinet, a ceiling fan, and custom barn doors. The impressive 8-foot by 6-foot walk-in closet has been professionally customized with built-in shelving and storage, offering exceptional organization. The oversized, insulated 3-car garage is a standout feature, boasting 11-foot ceilings, a 200-amp electrical service upgrade—perfect for EV charging, welding, or a workshop—pre-wiring for the third bay, and a keypad-entry garage door opener. Additional upgrades include a spacious laundry room with a double-basin stainless steel utility sink, an upgraded Samsung washer and dryer with steam features, a whole-house water filtration system requiring no filter changes, and a water softener. The exterior of the home has also been freshly painted, and the upgraded paver driveway and front porch add beautiful curb appeal. The value extends well beyond the upgrades. This home offers an incredible 2.7% FHA transferable interest rate—ask for details. For additional peace of mind, the air conditioning system has been fully serviced with maintenance components replaced and includes a one-year Del-Air warranty. Outdoor enthusiasts will appreciate being just moments from the community's beautiful 30-acre nature preserve, while Pear Park, located less than a quarter mile away, offers hiking trails, pickleball courts, and a dog park. Conveniently located near The Villages, you'll enjoy easy access to premier shopping, dining, golf, and entertainment. 5516 Windsong Oak Drive presents an exceptional opportunity to own a truly upgraded home in one of Lake County's most desirable communities.

5516 Windsong Oak Drive, Leesburg

3 Beds ⋅ 2 Baths ⋅ Leesburg Legacy Of Leesburg Unit 07 SubDv. ⋅ 34748 Zip Code

Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bath pool home in the sought-after 55+ gated community of Legacy of Leesburg! Offering 2,245 sq. ft., this home features an open floor plan, new luxury vinyl plank flooring, and a new A/C. The spacious kitchen includes a gas range and opens to the main living areas, making it ideal for entertaining. Step outside to your private screen-enclosed, solar-heated saltwater pool overlooking a peaceful pond with no rear neighbors. Additional features include plantation shutters, a gas dryer, and a screened garage door. Rare opportunity to assume the seller's low INTEREST mortgage (subject to lender approval and qualification). Enjoy resort-style amenities including a clubhouse, pool, tennis, fitness center, and a full calendar of activities—all conveniently located near shopping, dining, and medical facilities.

27127 Stoney Brook Drive, Leesburg

3 Beds ⋅ 2 Baths ⋅ Plantation At Leesburg Rosedown Village Lt SubDv. ⋅ 34748 Zip Code

Welcome to your dream home, located at The Plantation at Leesburg! This stunning updated home boasts serene golf course views and BRAND NEW APPLIANCES; which include Refrigerator, Dishwasher and Range in July 2026. As you walk through this beautifully maintained 3 bedroom/2 bathroom home which includes all the furniture, you will enjoy 1,897 sq ft of comfortable living space, while knowing the ROOF was replaced in October 2022, the HVAC in June 2024 and WATER HEATER in June 2024. This home offers an open floor plan with-in the living room/dining room and also has a family room located off of the kitchen; both great spaces for entertaining. The primary suite offers ample space, a walk in closet complete with a private en-suite bath complete with a walk-in shower along with a garden tub. The Plantation at Leesburg is an active 55+ community, with several amenities including 3 club houses, two 18 hole golf courses, 2 fitness centers, pickle ball, bocce ball, shuffleboard, softball/baseball fields, horseshoes, fishing and so much more; along with multiple clubs for you to join. This home truly has it all - style, space and the Florida lifestyle you have been dreaming of. Call for a private showing today.

24403 Amberleaf Court, Leesburg

3 Beds ⋅ 2 Baths ⋅ Pennbrooke Ph Q Sub SubDv. ⋅ 34748 Zip Code

Welcome to 842 Old Oaks Lane, a beautifully maintained custom home situated on a private lot in Pennbrooke Fairways, one of Central Florida’s premier gated 55+ communities. With peaceful conservation views and no rear neighbors, this inviting residence offers privacy, generous living spaces, and the relaxed Florida lifestyle. Step through the elegant leaded-glass front door into a bright, open floor plan featuring beautiful hardwood flooring, vaulted ceilings, plantation shutters in all of the bedrooms and expansive views toward the rear of the home. The spacious family room flows into the Florida room, creating an ideal setting for everyday living, entertaining, and enjoying the surrounding natural beauty. Chef inspired kitchen featuring abundant cabinetry, granite countertops, custom backsplash, stainless steel gas appliances, generous storage, and ample workspace. The thoughtfully designed floor plan includes a spacious primary suite with walk-in custom closets, vanity and shower, the second bedroom and custom full bath and shower that can easily function as a second primary suite, plus a separate den or home office with French doors. The expansive Florida room overlooking the conservation area is a true highlight, offering a peaceful setting to enjoy morning coffee, entertain friends, or simply appreciate the privacy and wildlife afforded by having no rear neighbors. Additional features include a 2018 roof, 2012 HVAC system, gas water heater, gas stove, interior laundry room, utility sink and cabinetry, oversized two-car garage, paver driveway and walkway, and mature landscaping. Pennbrooke Fairways offers three golf courses, recreation centers, swimming pools, fitness facilities, tennis and pickleball, clubs, social activities, and on-site dining, all conveniently located near The Villages. 842 Old Oaks Lane offers the space, privacy, and lifestyle that make Pennbrooke Fairways such a special place to call home.

842 Old Oaks Lane, Leesburg

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