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

Remarks: Welcome to Seasons at Hillside, in the lovely Sunnyside community. This beautiful ranch-style 4 bedroom, 2 bath home presents an open floor-plan with a living room and dining area. There is a screened-in patio, great for enjoying a relaxing morning cup of coffee or an evening to relax after a long day. A gorgeous kitchen with a center island, natural gas, and walk-in pantry. The primary bedroom is very spacious, with a walk-in closet, bathroom with double sinks, and an oversized modern shower. The other 3 bedrooms are a nice size with spacious closets. This lovely home is located close to restaurants and a few short miles from ViaPort. It's a short distance from UF Health and the Venetian Center. Only blocks away from the Sleepy Hollow Sports Complex, this home is positioned perfectly, for neighborhood walks, runs and bike rides. Built in 2022, the home is still like new. Very well maintained and ready for a new owner. Call today to set-up a showing. This one won't last long.

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Yolanda Presley, Llc (352-461-7241)

Remarks: Pre-Construction. To be built. Set within Oakstone Farms, a thoughtfully planned community surrounded by the beauty and recreation of Florida’s renowned Harris Chain of Lakes, this location captures the spirit of relaxed, active living. More than 50,000 acres of sparkling waterways stretch across eight scenic lakes connected by winding canals, creating endless opportunities for boating, fishing, and memorable days on the water. Within the neighborhood, dedicated greenspace, a dog park, and a tot lot provide inviting spaces to unwind and connect, while the charm of Mount Dora and Tavares brings boutique shopping, dining, and vibrant festivals nearby. Everyday conveniences are just minutes away in Leesburg, only 5.5 miles from the community, all complemented by a super low HOA. The Miramar reflects this lifestyle from the moment you arrive, with a driveway and entry adorned with brick pavers that set a welcoming tone. Step through the foyer to find 9'4" ceilings, crown molding throughout, and the Interior Trim Deluxe package, all combining to create an elegant and inviting first impression. The open floor plan flows seamlessly from room to room, with the great room bathed in natural light. Triple-panel patio doors extend the space to a 9'4" screened-in lanai, perfect for relaxing, entertaining, or enjoying the outdoors year-round. The chef-inspired kitchen blends style and functionality with a large granite-topped island, tile backsplash, stainless steel appliances including a gas range, and a spacious pantry. Whether preparing meals, hosting gatherings, or enjoying casual dining, this space is designed to accommodate it all. Tucked privately at the rear, the primary suite provides a serene retreat with a generous walk-in closet and a spa-inspired bath featuring an oversized tiled shower and a conveniently placed linen closet. Three additional bedrooms are positioned near the foyer, including one with a private bath for guests or a personalized space such as a home office or fitness room. A secondary bathroom includes a tiled shower and tub combination. Everyday convenience continues with a centrally located laundry room with washer and gas dryer included, alongside a built-in Smart Home Package featuring a Ring Video Doorbell, smart thermostat, keyless entry smart door lock, and Deako switches. The spacious two-car garage offers ample storage, while the full builder warranty provides peace of mind. With its thoughtful design, seamless indoor-outdoor living, and access to the natural beauty and recreational lifestyle of Oakstone Farms and the Harris Chain of Lakes, the Miramar perfectly blends comfort, style, and Florida living at its finest.

Listing is courtesy of: NEW HOME STAR FLORIDA LLC (407-803-4083)

Listing Agent: Charles Pennant (407-305-4317)

Remarks: Pre-Construction. To be built. Set within Oakstone Farms, a thoughtfully planned community surrounded by the beauty and recreation of Florida’s renowned Harris Chain of Lakes, this location captures the spirit of relaxed, active living. More than 50,000 acres of sparkling waterways stretch across eight scenic lakes connected by winding canals, creating endless opportunities for boating, fishing, and memorable days on the water. Within the neighborhood, dedicated greenspace, a dog park, and a tot lot provide inviting spaces to unwind and connect, while the charm of Mount Dora and Tavares brings boutique shopping, dining, and vibrant festivals nearby. Everyday conveniences are just minutes away in Leesburg, only 5.5 miles from the community, all complemented by a super low HOA. The Miramar reflects this lifestyle from the moment you arrive, with a driveway and entry adorned with brick pavers that set a welcoming tone. Step through the foyer to find 9'4" ceilings, crown molding throughout, and the Interior Trim Deluxe package, all combining to create an elegant and inviting first impression. The open floor plan flows seamlessly from room to room, with the great room bathed in natural light. Triple-panel patio doors extend the space to a 9'4" screened-in lanai, perfect for relaxing, entertaining, or enjoying the outdoors year-round. The chef-inspired kitchen blends style and functionality with a large granite-topped island, tile backsplash, stainless steel appliances including a gas range, and a spacious pantry. Whether preparing meals, hosting gatherings, or enjoying casual dining, this space is designed to accommodate it all. Tucked privately at the rear, the primary suite provides a serene retreat with a generous walk-in closet and a spa-inspired bath featuring an oversized tiled shower and a conveniently placed linen closet. Three additional bedrooms are positioned near the foyer, including one with a private bath for guests or a personalized space such as a home office or fitness room. A secondary bathroom includes a tiled shower and tub combination. Everyday convenience continues with a centrally located laundry room with washer and gas dryer included, alongside a built-in Smart Home Package featuring a Ring Video Doorbell, smart thermostat, keyless entry smart door lock, and Deako switches. The spacious two-car garage offers ample storage, while the full builder warranty provides peace of mind. With its thoughtful design, seamless indoor-outdoor living, and access to the natural beauty and recreational lifestyle of Oakstone Farms and the Harris Chain of Lakes, the Miramar perfectly blends comfort, style, and Florida living at its finest.

Listing is courtesy of: NEW HOME STAR FLORIDA LLC (407-803-4083)

Listing Agent: Charles Pennant (407-305-4317)

Remarks: Short Sale. Short Sale! Welcome to this charming, well-maintained 4-bedroom, 3-bath home with over 2,100 sq ft in Leesburg! This property offers a comfortable and inviting layout, perfect for both everyday living and entertaining. Step inside to find brand-new carpet in the bedrooms, adding a fresh and cozy feel, while the living room and main areas feature tile flooring for easy maintenance and a clean, modern look. The living spaces are bright and welcoming, creating a warm atmosphere for you and your guests. Enjoy the outdoors in your fully fenced backyard, offering privacy and plenty of space to relax or entertain. A beautiful play set is already in place, making it a perfect setup for families or anyone who loves outdoor living. The home has been well cared for, including a well-maintained A/C system, providing comfort and peace of mind. Conveniently located near shopping, dining, and major roadways, this home combines comfort, value, and location. Don’t miss this great opportunity—schedule your showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Nancy Tanago (407-556-5936)

Remarks: Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ This adorable Leesburg home is proof that character never goes out of style! Opportunity is knocking on Wilson Avenue where FRESH INTERIOR PAINT (2026) gives the home a bright, fresh feel, and the NEWER ROOF (2021) adds peace of mind. Set on a spacious .22 ACRE LOT, FULLY FENCED with NO HOA, this single story concrete block home delivers both space and flexibility in a quiet, established community tucked away against the shores of LAKE HARRIS and the HARRIS CHAIN OF LAKES. Mature trees, landscaping and welcoming curb appeal set the tone, while the 1-car garage offers convenient parking or additional storage. Inside, the home is full of warmth and personality with ORIGINAL HARDWOOD FLOORS, a cozy FIREPLACE in the living room, and an easy flow between the OPEN LIVING & DINING spaces. The kitchen offers tons of cabinet storage and charming vintage vibes, along with a casual breakfast nook perfect for everyday meals or morning coffee. The SPLIT BEDROOM layout adds privacy, and both bedrooms feature their own en-suite baths – a rare find in homes of this size. The PRIMARY SUITE includes a WALK-IN CLOSET, creating a comfortable retreat at the end of the day. Step outside to enjoy the large fenced backyard, offering plenty of room for pets, gardening, outdoor entertaining or future plans. The location adds even more appeal – just two blocks from Palmar Park, minutes to the historic downtown Leesburg district, and conveniently close to US-27 and US-441 for easy commuting. Shopping, dining, waterfront parks and the Chain of Lakes lifestyle are all at your fingertips! Whether you are looking to downsize your primary residence, a first home with character and room to make it your own, or a solid investment, this Leesburg property offers charm, location and great potential all in one. Call today to schedule your tour!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Architectural character and resort-style outdoor living come together on this beautifully maintained .43-acre corner lot located in a golf cart-friendly community with NO HOA. From the moment you arrive, the striking floor-to-ceiling stone chimney, bold architectural beams, and fresh exterior paint (2025) create standout curb appeal and give this home a custom feel you do not see every day. Inside, vaulted ceilings with exposed wood beams and a dramatic stone fireplace anchor the living space, while clerestory windows bring in natural light and enhance the open feel. Durable luxury vinyl plank flooring runs throughout the main living areas, offering the look of hardwood with easy maintenance and long-term durability. A built-in wet bar adds both function and personality, making the space ideal for entertaining. This is not a cookie cutter home. The architectural details and thoughtful layout set it apart from the typical floor plan. The split-bedroom design provides privacy, with an oversized primary suite offering generous closet space and an en-suite bath, while two additional bedrooms are positioned on the opposite side of the home near a full bath and laundry area. The kitchen features solid wood cabinetry, stainless steel appliances, a breakfast nook, and convenient access to the dining room for an easy flow. The backyard is a true highlight, featuring an impressive screened patio and pool enclosure with a fully pavered deck, multiple seating areas, and a covered lanai complete with ceiling fan and dedicated grilling space. The resurfaced gas-heated pool (2025) includes a new salt chlorination system (2025) and is connected to city gas for efficiency and convenience. Major updates include a new roof (2026), new pool screen enclosure (2026), exterior paint (2025), two AC units with one replaced (2017) and one replaced (2022), and a new drain field (2021). The oversized garage provides additional storage or workspace flexibility. With nearly half an acre, distinctive architectural detail, durable finishes, and extensive system upgrades, this home offers space, personality, and functionality in one complete package.

Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE (800-948-0938)

Listing Agent: Breanna Eckerdt (352-901-4464)

Remarks: Discover a quietly impressive four-bedroom, two-bath pool home designed for comfortable living and effortless everyday enjoyment. A screened front porch welcomes you inside, where the spacious main living area opens to a spacious kitchen featuring granite counters, an island with breakfast bar, generous pantry storage, and a bright eat-in nook. Just off the kitchen, a large laundry room offers additional convenience, with the washer and dryer thoughtfully included. The kitchen flows seamlessly into the living room, creating an easy gathering space that extends out to a screened patio running the full length of the home—ideal for relaxing or entertaining. The primary suite offers a large walk-in closet and private bath. Two additional bedrooms also feature walk-in closets, and the fourth includes a full-length closet, providing exceptional storage throughout. A dedicated linen closet in the second bath adds even more usefulness. Outside, a large fenced yard hosts an above-ground pool with surrounding deck, plus a unique two-story structure offering abundant open storage below and a framed-in upper level with its own balcony—ready for customization as a workshop, studio, or retreat. With no HOA, there’s room to bring your boats, RVs, and other toys. A property with this much space and potential is a rare find. Schedule your showing and experience it for yourself.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Barrett Spray (407-927-3650)