Homes for Sale Near Oak Park Middle in Leesburg - 67 homes

Remarks: Under contract-accepting backup offers. This charming property at 109 N Oakland Street offers a prime location just steps from historic downtown Leesburg. With its inviting curb appeal and classic Florida character, the property is functional and well maintained. The home sits on a spacious lot and provides easy access to Leesburg’s growing downtown district, where you’ll find boutique shops, restaurants, lakefront parks, and community events year-round. Inside, the property maintains its traditional charm while offering functional living areas filled with natural light. The flexible layout makes it a great option for a buyer looking to customize and add value. Outside, the yard provides ample space for outdoor enjoyment, gardening, or future improvements along with a complimenting workshop in the backyard. Located within minutes of Lake Harris, Venetian Gardens, and major roadways like US-441, this property combines convenience with small-town charm. Whether you’re seeking an affordable home close to downtown or a smart investment in a growing area, 109 N Oakland Street delivers excellent potential.

Listing is courtesy of: RLW REALTY (352-771-2560)

Listing Agent: Logan Wilson (352-771-2560)

Remarks: OPPORTUNITY JUST KNOCKED - 20K LOUDER! Big home, big lot, BIG $20K price drop—this one just became the best value in the subdivision. Welcome to a home that truly lives large—inside and out. Set on an impressive .34-acre corner lot, this sprawling residence is one of the largest homes with one of the biggest lots in the neighborhood, offering room to spread out, entertain, and live comfortably for years to come. From the moment you step into the two-story foyer and living room, the sense of openness is undeniable, with soaring ceilings that set the tone for the generous layout throughout. The first floor offers incredible flexibility, including an extra-spacious bedroom and the potential for an in-law or multi-generational living setup. Upstairs, a bright bonus office or loft overlooks the living area through thoughtfully added windows—maintaining the open feel while creating a perfect space for work, play, or relaxation. Storage is abundant at every turn—this home was designed with space in mind. At the heart of the home is a gourmet kitchen built for entertaining, complete with double ovens, a gas stove, TWO refrigerators, large decorative tile, a cozy dinette area, and a separate formal dining room for hosting memorable gatherings. Upstairs, the primary suite is a true retreat, featuring an en-suite layout that flows into a large bathroom and two separate walk-in closets—plenty of room for all your Florida lifestyle essentials, especially when you’re living near the Chain of Lakes. Now let’s talk about the backyard—because this is where the fun happens. Fully fenced, beautifully spacious, and rarely found at this size, the outdoor area offers endless possibilities: gatherings, play, pets, gardening, or simply enjoying the Florida sunshine. The screened-in lanai is perfect for year-round relaxation or entertaining, while the extended concrete patio expands your outdoor living space even further. This is the kind of backyard that invites memories. Additional highlights include a newer upstairs A/C (2024), epoxy garage floors, and thoughtful upgrades throughout. Located in a quiet neighborhood, you’re just minutes from the beauty of Venetian Gardens, nestled between Lake Harris and Lake Griffin, and close to everything Leesburg has to offer. Enjoy a charming downtown filled with local restaurants and shops, easy access to US-441 and US-27, proximity to Sleepy Hollow Sports Complex, Leesburg Hospital, Lake Square Mall, and nearby colleges including Lake-Sumter State College and Beacon College. Whether your lifestyle calls for space, convenience, entertaining, or simply room to breathe—this home delivers it all. Plenty of room, plenty to do, and a location that truly connects you to the best of Leesburg living.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: Carrie Pappas (352-460-1109)

Remarks: Impeccably maintained villa that has undergone an extensive renovation, offering an almost-new living experience. Interior updates include recessed lighting with dimmers in the living areas and garage, all-new drywall in the living area and garage, new flooring throughout, and a fully updated kitchen. The home features four new skylights and a new roof, creating a bright and inviting Florida atmosphere. Mechanical and structural improvements include a new HVAC system, new electrical panel, new natural gas fireplace, new washer and dryer, new garage door, and a hot water tank (2025). The bathroom has also been updated for a clean, modern presentation. A lovely courtyard provides an ideal outdoor living space, perfect for relaxing or entertaining. The HOA offers excellent value with low fees, covering termite protection, exterior maintenance, irrigation, and a roof reserve for future replacement. Low taxes further enhance the affordability of this nearly fully renovated Florida home. This villa reflects exceptional care and thoughtful upgrades throughout, offering true move-in readiness.

Listing is courtesy of: REAL PROPERTY INTERNATIONAL (407-909-8000)

Listing Agent: Bob Levy, Sr. (407-509-8255)

Remarks: Welcome home to this well maintained, LIKE NEW one-story retreat nestled on a quiet interior lot in Leesburg’s Lake Denham Estates. Inside you're greeted with soaring ceilings and an abundance of natural light, creating an airy atmosphere complemented by a neutral color palette and wood look tile flooring. Centering the open floorplan in the eat-in kitchen complete with granite countertops, SS appliances, farmhouse sink and a walk-in pantry; flows seamlessly into the family room, offering the perfect layout for both daily living and effortless entertaining. The thoughtful split floorplan prioritizes privacy, positioning the two spacious guest bedrooms away from the primary suite, which has its own ensuite with dual vanity, tile shower and walk-in closet. Outside, the expansive backyard is a rare find, featuring a covered patio and NO rear neighbors. Ideally located, you are just minutes from the community pool, playground, and the boat ramps at Griffin State Park, with quick access to major transportation routes for an easy commute. This home will not last, Tour today!

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Jo Holton (307-690-7219)

Remarks: REDUCED - Spacious 2BR/2.5BA Home on Prime Corner Lot - Discover comfort and versatility in this generously sized home featuring 2 bedrooms, 2.5 baths, and an additional 11x16 flex room—perfect as a home office, cozy den, or third bedroom. The open-concept kitchen flows seamlessly into the Great Room and breakfast nook, with a convenient walk-through to the formal dining area. Large lanai is enclosed with vinyl windows. 3 sets of stacking sliding doors to enclosed porch. Half bath is adjacent to the inside utility area. Oversized garage. Floors in home are waterproof. New roof in August 2025. Almost all the furniture is negotiable. Duchess model - but larger

Listing is courtesy of: BONJORN REAL ESTATE (352-394-2112)

Listing Agent: Pamela Bonjorn (352-267-6003)

Remarks: MOTIVATED SELLER!!! JUST REDUCED!!! Bring all offers for this MOVE IN READY HOME!!!! Discover this amazingly well maintained one-owner home—a spacious 4-bedroom, 2-full-bath single-family home offering 1,809 sq ft of comfortable living space. Pride of ownership shines throughout, with major updates already taken care of: a new roof installed in March 2023. A new water heater replaced 1 year ago, complete new A/C system April 2016. Enjoy serene, private views from your back yard on your screened patio overlooking a tranquil pond and backed by a mature nature conservation area—ensuring no rear neighbors. Endless natural beauty right outside your door. Fully irrigated lawn. Perfect for families seeking peace, privacy, and move-in-ready convenience. Don't miss this rare opportunity!

Listing is courtesy of: BONJORN REAL ESTATE (352-394-2112)

Listing Agent: Genger Narehood (352-394-2112)

Remarks: One or more photo(s) has been virtually staged. Under Construction. Ready for the Florida lifestyle? You'll love living at Silver Lake Pointe, where you'll be just minutes from all the shopping, dining, and entertainment options, with the convenience of downtown Leesburg and Mount Dora nearby. Plus, you'll have three major lakes and beautiful Silver Lake right in your backyard, along with numerous parks and golf courses nearby offering endless recreational opportunities. Then, get ready to enjoy sunny days with the community amenities, including a swimming pool, cabana, and playground. Your dream home awaits at Silver Lake Pointe! The Linden offers the perfect layout and smart storage solutions for every homeowner. The main floor features an open-concept kitchen with an island and an oversized pantry, a spacious living room, a dining area, and a versatile flex room (an ideal space offering ample storage and functionality), plus a convenient bathroom. Enjoy your outdoor space on the patio and take in the Florida sunsets. Upstairs, a spacious loft provides a comfortable area for entertaining. Down the hall, you'll find three guest bedrooms, a shared bathroom with a double vanity, and a laundry room. The expansive primary suite offers plenty of space with a huge walk-in closet, a private bathroom with a shower, and two linen closets. The Linden's impressive use of space makes this single-family home welcoming and livable, with all the advantages of a Stanley Martin home.

Listing is courtesy of: SM FLORIDA BROKERAGE LLC (770-365-2982)

Listing Agent: Jason Walzer (407-537-2883)

Remarks: Price Reduced! NEW ROOF! This beautifully landscaped property offers a 3-bedroom, 2-bath split floor plan with an open-concept layout, outfitted with crown molding and designed for modern living. The master suite is a private retreat, featuring a walk-in shower, double vanity, and a custom walk-in closet with a organized well thought out closet system. The gourmet kitchen boasts a large island with granite countertops, solid wood cabinets, stainless steel appliances, and stylish backsplash, complemented by a breakfast nook. With plenty of room the separate but (still visbile) living and dining rooms makes it great for entertaining. There is also a spacious bonus room ideal for a family room, media room, office or can even be converted into a 4th bedroom. Additional highlights include a laundry room with abundant storage, water softener, and a 2-car garage. Relax year-round in the enclosed patio under air, complete with walls of windows for natural light and motorized shades for privacy. Arlington Ridge is a 24-hour gated and guarded community offering championship golf, resort-style amenities, and low-maintenance living. HOA fees cover lawn care, high-speed internet, cable, and full use of amenities including two pools, hot tub, fitness center, movie theater, and more. Dine at the Chesapeake Grill & Tavern, enjoy walkable streets with sidewalks and lighting, and take advantage of the community’s prime central location—just minutes to shopping, restaurants, and healthcare, with easy access to Orlando, airports, and Florida’s coasts. Don’t miss this neighborhood gem—schedule your private showing today!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Raymond Reyes (407-243-8940)

Remarks: Located in the desirable Sunnyside area, this stunning retreat like property is tucked behind a private electric gated entrance and offers both luxury and functionality with beautiful views of the pool and backyard oasis. The spacious kitchen is designed for both everyday living and entertaining, featuring abundant cabinetry, granite countertops, a large island, gas range, double ovens, and a sink perfectly positioned to overlook the backyard through expansive glass windows. The inviting family room features a gas fireplace, while the main living room includes in ground outlets for flexible furniture placement. The massive primary suite offers private doors leading to the pool area along with two walk-in closets. The luxurious primary bath includes dual vanities with a makeup area, walk-in shower, garden tub, and private water closet. An office with built-ins provides the perfect workspace, and the home offers numerous storage closets throughout. Bedrooms two and three share a Jack-and-Jill bathroom with dual sinks and a tub/shower combination, while the fourth bedroom has convenient access to a pool bath featuring a walk-in shower. Upstairs, a versatile loft with a half bath and closet can serve as a playroom, game room, or private suite. The garage entry leads into a convenient laundry and mud room with built-in cubbies for added organization. 39x22 garage includes a workbench and sink, ideal for projects or additional workspace. Step outside to your private outdoor retreat featuring a pool and hot tub with water features and a fully equipped summer kitchen, creating the perfect setting for relaxing or entertaining. New roof & gutters in 2021, new pool equipment & brick paver sidewalk.

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-787-6966)

Listing Agent: Craig Yox (352-255-6002)

Remarks: Escape to your own private lakefront countryside retreat with this picturesque pond-front property set on 8± acres, offering incredible equestrian potential and peaceful, open space. This charming 5-bedroom, 2.5-bath ranch-style home spans 2,381 square feet and is perfectly positioned with a generous setback, creating a serene sense of arrival through the expansive front yard. Designed for both comfort and functionality, the property features two cross-fenced pastures shaded by mature trees, a garden area, a large parking pad, and a 20x20 metal carport with a workshop. A paver walkway leads to the inviting front porch—an ideal spot to unwind with morning coffee or enjoy a refreshing drink on a warm afternoon. Inside, vaulted ceilings and low-maintenance tile flooring enhance the bright, open-concept layout. The living room centers around a cozy wood-burning fireplace and flows seamlessly into the kitchen and dining areas, creating the perfect space for everyday living and entertaining. The kitchen is well-equipped with abundant wood cabinetry, stainless-steel appliances—including a French-door refrigerator—and a convenient breakfast bar for casual gatherings. Double French doors open to a spacious Florida room, where panoramic windows invite in natural light, backyard views, and gentle breezes. The primary suite offers a relaxing retreat with a walk-in closet and a private en-suite bath featuring dual sinks and a walk-in shower. Four additional bedrooms provide flexibility for family and guests, and the home also features a dedicated home office. Additional highlights include a laundry room, an oversized storage space currently used as a pantry, a whole-house surge protector, a newer A/C system, a whole-house filtration water softener, and a durable metal roof—ensuring both comfort and peace of mind. Outdoors, the property continues to impress with a variety of fruit trees, a storage shed, and a second metal carport ideal for boats or extra vehicles. A small barn offers excellent potential for conversion into horse stables. Wander to the back of the property to discover Lake Robinson nestled beneath a canopy of mature trees—your own private fishing and relaxing escape. Whether you're an equestrian enthusiast or simply seeking space, privacy, and natural beauty, this exceptional property offers the perfect place to call home.

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-735-4433)

Listing Agent: Loretta C. Maimone (352-357-2400)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Experience the ultimate Florida lifestyle at 27014 Camerons Run in the premier 55+ community of Arlington Ridge. This meticulously maintained residence is now an even more exceptional value: the seller will prepay your HOA fees for TWO FULL YEARS! This incredible incentive saves you $127 per month, allowing you to enjoy world-class amenities with zero carrying costs for your first 24 months. Step inside to an open, sun-drenched floor plan featuring modern finishes and a seamless flow perfect for entertaining. The spacious kitchen and inviting living areas overlook a private outdoor space, ideal for morning coffee or sunset views. Residents enjoy access to a championship golf course, resort-style pools, a fitness center, and on-site dining. With your HOA fees covered, you can dive straight into the social clubs and active lifestyle that make Leesburg famous. Don’t miss this rare opportunity to secure a "worry-free" move-in with significant immediate savings. Welcome home!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Jessica Collins (386-564-0120)

Remarks: Welcome to Chesterbrook — a quiet, well-kept 55+ community just minutes from Lady Lake, The Villages, and the sparkling waters of Lake Griffin on the renowned Chain of Lakes. This beautifully updated 2-bedroom, 2-bathroom ground-floor condo offers comfort, convenience, and a relaxed Florida lifestyle. Step inside to an inviting open floor plan with premium ceramic tile in the kitchen, baths and living areas for added durability and style. As an end-unit you will enjoy extra privacy and a peaceful setting. The enclosed patio provides the perfect spot to unwind on warm afternoons — a cozy indoor-outdoor retreat you can enjoy year-round. Parking is just steps from your front door, making daily living effortless. Chesterbrook residents enjoy a friendly, active community with amenities that include: A refreshing community pool A welcoming clubhouse A convenient bathhouse Shuffleboard courts for leisurely afternoons You’ll love the unbeatable location — close to restaurants, shopping, medical facilities, and only a short 15-minute drive to all the entertainment and conveniences of The Villages. Outdoor lovers will appreciate quick access to the Chain of Lakes for boating, fishing, and scenic adventures. The condo fee covers water, sewer, trash, and grounds maintenance, giving you true low-maintenance living. Community roof replacement is already underway. Whether you’re looking for a comfortable full-time home or a smart investment opportunity, this move-in-ready condo checks all the boxes. Come see why Chesterbrook is such a special place to call home.

Listing is courtesy of: RE/MAX PREMIER REALTY (352-735-4060)

Listing Agent: James Donovan (352-552-8195)

Remarks: Price reduced $5,000. Situated by the serene Lake Denham and completed in 2022, this 3 bedroom, 2 bathroom home seamlessly combines modern architecture with the tranquility of nature. Step inside to discover luxury vinyl plank flooring and an expansive open layout, ideal for socializing and entertaining. The kitchen, equipped with stainless steel appliances and lavish granite countertops, is a haven for both cooking enthusiasts and gracious hosts. A fully fenced backyard offers added privacy and a perfect setting for relaxed outdoor living. With its blend of contemporary style and natural beauty, this home offers unparalleled comfort and sophistication. The Lake Denham community offers residents a sparkling pool for relaxation, an outdoor gym for fitness enthusiasts, and a playground for fun. Don't miss the chance to make this extraordinary property your dream home!

Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)

Listing Agent: Michael Kushner (516-510-7218)

Remarks: One or more photo(s) has been virtually staged. Move-In Ready New Construction Home in Fox Pointe – Leesburg, FL Discover comfort, style, and energy efficiency in this beautifully designed 1-story, 4-bedroom, 2-bathroom home with 1,840 square feet of living space and a 2-car garage, located in the boutique Fox Pointe community—a quiet enclave of just 42 homesites near US-27 and the Harris Chain of Lakes Boat Ramp. Interior Highlights • White shaker cabinets with elegant crown molding for a clean, timeless look • Quartz countertops in both kitchen and bathrooms for durability and style • Engineered Vinyl Plank flooring in all main living areas; plush carpet in bedrooms for added comfort • Stainless steel GAS appliances including range, microwave, dishwasher, and refrigerator • Gas Tankless Water Heater and gas dryer hookup for energy-conscious living • Washer, dryer, and blinds included—move in with ease! ??? Open-Concept Living • Spacious kitchen island with counter-height bar seating—perfect for casual dining or entertaining • Kitchen opens to the dining area and expansive Great Room, creating a seamless flow • Kitchen sink overlooks the backyard and living space, ideal for hosting and everyday living Energy Efficiency & Wellness • Energy Star Certified with spray foam insulation and fresh air intake system • Designed to reduce allergens, improve indoor air quality, and lower utility bills • A healthier, quieter, and more energy-efficient home for modern Florida living Community & Location Perks • Fox Pointe amenities include a dog park and open green space for outdoor enjoyment • Minutes from Harris Chain of Lakes—boating, fishing, and waterfront fun await • Close to Publix, restaurants, and shopping, including a brand-new Aldi just down the street • Easy access to Downtown Leesburg, Venetian Gardens, Lake Griffin State Park, and Lakeridge Winery • Enjoy nearby golf courses, nature trails, and community events throughout Lake County Property Features • 4 Bedrooms 2 Bathrooms 2-Car Garage 1,840 Sq Ft • Located in a small, close-knit community with limited availability This home is truly MOVE-IN READY—perfect for anyone seeking a low-maintenance, high-comfort lifestyle in Central Florida.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Tina Bircher (321-228-4267)

Remarks: Custom built home boasting a perfect blend of luxury and classic elegance. This luxurious 4 bedroom, 3 bathroom home is located in the sought after gated community of Majestic Oaks. As you enter the home through the French doors, you will notice the tall ceilings throughout the home and the open floor plan that seamlessly connects the living, dining, and custom kitchen areas. The kitchen boasts a large quartz waterfall island, tall cabinets, double oven, and French door refrigerator. The laundry room includes a separate pet wash station. The outdoor screened in patio is perfect for early morning coffee or late night relaxation. Home includes a whole house water softener and a 10' X 16" storage shed. The shed is prewired for electricity if desired and the yard is completely fenced in.

Listing is courtesy of: BLUE WATER REALTY INVESTMENTS (407-957-7581)

Listing Agent: James Brown (407-456-4907)

Remarks: Don’t miss this rare opportunity to own a pristine, move-in-ready sanctuary in the highly desirable Lake Denham Estates neighborhood. This charming home is the perfect blend of modern comfort and effortless Florida living, featuring a bright, open-concept design that invites natural light and easy flow throughout. The heart of the home is a beautifully updated kitchen with sleek granite countertops, rich dark-wood cabinetry, stainless steel appliances, and a generous island that doubles as the ideal gathering spot for casual meals or entertaining. It opens seamlessly into the dining and living spaces, creating the perfect backdrop for everything from relaxed weeknights to weekend gatherings. Your private primary retreat offers a peaceful escape with ample space and a bath featuring granite finishes. The additional bedrooms provide flexibility for guests or a home office. Outside, enjoy your own private backyard oasis complete with a spacious concrete patio, the ideal setting for morning coffee, evening gatherings, or simply unwinding under the Florida sky. The fully fenced yard also adds peace of mind. The home is conveniently located with easy access to major highways, shopping, dining, and all that Leesburg and Central Florida have to offer, this beautifully maintained home represents outstanding value and true move-in readiness in today’s market. Properties like this in Lake Denham Estates move quickly. Schedule your private showing today before it is too late!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Jerry Miller (407-480-9633)

Remarks: Fully renovated 2007 mobile home with 4 bedrooms, 2 bathrooms, and 2052 sq ft on a .25-acre corner lot. Features include an open floor plan, new 2025 roof, new LVP flooring, fresh interior paint, new interior and exterior doors, stunning kitchen with new soft close cabinets, granite countertops, and brand new stainless steel appliances. Move in ready!

Listing is courtesy of: LISTED SIMPLY (800-995-5879)

Listing Agent: Sinan Zakaria (800-995-5879)

Remarks: Experience comfort, security, and modern convenience in this beautifully upgraded single-family home located in the desirable 55+ community of Arlington Ridge in Leesburg, Florida. This home features Wi-Fi–enabled appliances, an Ecobee smart thermostat, and Wi-Fi–controlled sprinklers, making it easy to monitor and manage the home from anywhere. Additional interior highlights include QUARTZ countertops throughout, soft-close cabinetry, stainless steel NATURAL GAS appliances, rounded wall corners, elegant archways, and a CENTRAL VACUUM SYSTEM . A 50-gallon commercial-grade water heater provides reliable performance for everyday living. Built in 2021, this home is equipped with premium upgrades designed for peace of mind, including a Generac whole-home GENERATOR, upgraded 16-seer AC, dual-pane Aragon glass windows with low-e tint glass coating, a whole-home WATER FILTRATION SYSTEM, and water softener. The epoxy-finished garage floor adds durability and a clean, finished look. Every detail has been thoughtfully selected to support both comfort and low-maintenance living. Located in an active 55+ community, residents enjoy resort-style amenities and a vibrant social environment. Community features include a 18-hole golf course, tennis and pickleball courts, bocce ball, a fitness center, sauna, fitness and recreation pools, spa, and an on-site restaurant, pub and movie theatre. Daily activities, clubs, and events provide endless opportunities to stay active, social, and engaged. Your quarterly HOA fee includes cable, internet and lawn care. This home offers the perfect blend of modern upgrades and a lifestyle centered around relaxation and recreation.

Listing is courtesy of: HAMMOND REALTY GROUP LLC (407-468-0074)

Listing Agent: Diana Hammond (407-276-4420)

Remarks: Welcome to lakefront living on Lake Griffin, part of the Harris Chain of Lakes. This beautifully updated home offers the perfect blend of modern comfort and classic Florida lake life. Originally renovated in 2020, the interior features LVP flooring throughout, an open concept kitchen with stone countertops, tile backsplash, updated bathrooms designed for both style and function, spacious bedrooms for visitors or every day use, and multiple seating rooms for all your needs. Step outside to your new Trex screened-in porch overlooking the water, brick-paved pergola with built in grill and fire pit area, plenty of green space for game nights and your new private electric dock that makes boating, fishing, and exploring the Harris Chain effortless. Recent improvements include Hardie board siding, roof, a new well, sea wall, and water purification system, offering peace of mind and low-maintenance waterfront living. Even better, the home is being offered fully furnished with modern furnishings, making this a truly turnkey opportunity whether you're looking for a primary residence, weekend retreat, or Florida lake escape.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Nia Medina (612-388-0431)

Remarks: The Plantation at Leesburg a gated golf community ! 2BR/2BA Home with vaulted ceiling, wood laminte flooring and eat-in-kitchen.

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-787-6966)

Listing Agent: Jessica Sanchez, Pa (352-504-7772)