Homes for Sale Near Leesburg High in Leesburg - 103 homes

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)