Leesburg FL Historical Real Estate, Homes for Sale

6 Beds ⋅ 3 Baths ⋅ Indian Hill SubDv. ⋅ 34748 Zip Code

Investor opportunity in Leesburg, Florida. This fully rented single-family property offers three separate income-producing spaces, including a pool home, providing immediate rental performance from day one. The property is turnkey with stable tenants in place, partial interior updates, and a 30-day notice requirement for renewals or non-renewals. Utility, lawn, pool, and internet services are already incorporated into the operating structure for easy management. Located in the heart of Leesburg near Downtown Leesburg, Lake Harris, Venetian Gardens, UF Health Leesburg Hospital, Highway 27, and local retail and employment centers, this area continues to show strong rental demand and consistent occupancy. This is a rare chance to acquire a centrally located income-producing property in an established Lake County rental corridor. Financials and full property details available upon request. Property is being sold with tenants in place. Showings by appointment only.

1611 Indian Trail, Leesburg

$359,999

3 Beds ⋅ 3 Baths ⋅ Golfview Sub SubDv. ⋅ 34788 Zip Code

Virtually Staged. Peaceful, majestic oak trees greet you as you arrive at this warm and welcoming home, offering nearly 2,300 square feet of comfortable living space designed for both everyday living and unforgettable gatherings. Inside, generously sized rooms create an inviting atmosphere, with oversized living and dining areas perfect for hosting holidays, celebrations, and quiet evenings with loved ones. The eat-in kitchen becomes the natural gathering place, where meals are shared and memories are made. Step outside to rear decks and imagine weekend barbecues, morning coffee, or unwinding as the sun sets in the distance. Set on a generous, fenced lot of nearly half an acre with no HOA, this property offers rare privacy, flexibility, and room to enjoy the outdoors—whether for pets, play or future projects. Home is ideally located just minutes from dining, shopping, and local conveniences, this inviting 3-bedroom, 2.5-bath home is a peaceful retreat in a prime location, ready for you to make it your own. Note: Recent housing development behind property has created a beautiful Water View Buffer at the rear of the home! Make your viewing appointment to see this home today! RV/EV 40 amp outlet installed by driveway, Trane HVAC system installed 2020, re-roofed in 2020, new water heater 2026, septic system recently inspected and pumped. All information recorded in the MLS is intended to be accurate however, it should be independently verified by buyer and their agent.

34041 Highland Road, Leesburg

$210,000

3 Beds ⋅ 2 Baths ⋅ Hollywood Heights SubDv. ⋅ 34748 Zip Code

Under contract-accepting backup offers. This home is everything you've been looking for in Leesburg Fl. The renovations made in 2021 include a new roof, fresh interior and exterior paint, updated electrical (tested by a licensed master electrician), and a fully serviced HVAC system by a licensed professional, refinished cabinetry, countertops, range and range hood. Both bathrooms have been updated with refinished tile, new vanities, sinks, mirrors, lighting, toilets, and luxury plank flooring back in 2021. All three bedrooms offer new carpet and lighting, and new interior doors have been installed throughout the home. Updated lighting was added in every room except for the unique and stylish living room fixture. The spacious primary bedroom offers excellent privacy. Located within walking distance to Leesburg Elementary and Oak Park Middle School, this property offers both comfort and convenience. Don’t miss this opportunity! Schedule your private showing today!

804 S Lone Oak Drive, Leesburg

$269,000

4 Beds ⋅ 2 Baths ⋅ Orange Heights SubDv. ⋅ 34748 Zip Code

Under contract-accepting backup offers. Welcome to this comfortable 4-bedroom, 2-bath home offering a practical layout and inviting atmosphere. The 10-foot ceilings elevate the main living areas, creating a sense of openness and space while maintaining a warm, homey feel. A two-car garage provides everyday convenience and storage. Outside, enjoy a generously sized backyard with a refreshing pool — perfect for enjoying Florida weather, outdoor gatherings, or simply relaxing in your own private space. The property also benefits from an alleyway behind the home, offering additional separation and privacy from neighboring homes, giving the yard a more open and roomy feel. Conveniently located near downtown Leesburg, this home offers quick access to local shops, restaurants, parks, and community events. Everyday essentials and major roadways are just minutes away, making this a great spot for those seeking comfort, convenience, and a welcoming neighborhood feel.

207 N Perkins Street, Leesburg

$239,990

4 Beds ⋅ 2 Baths ⋅ Leesburg Liberia SubDv. ⋅ 34748 Zip Code

Under contract-accepting backup offers. REDUCED!!!! Welcome to this beautifully REMOLDED gem in the heart of Leesburg, Florida — a rare opportunity for move-in ready living paired with an unbeatable location. Features a fresh interior from top to bottom: new flooring, modern light fixtures, updated kitchen cabinetry and countertops, contemporary baths, and a full palette of neutral finishes designed for today’s lifestyle. Step outside to a manageable, landscaped yard with mature trees and a welcoming front porch—perfect for morning coffee or relaxed evenings. Inside, you’ll find an open dining/living flow ideally suited for everyday living and entertaining. Additional highlights include generous closet/storage space, convenient laundry area, and a newly upgraded HVAC system for comfort and efficiency. Situated in Leesburg’s charming community, just minutes from shopping, dining, major retail, and everyday convenience. Downtown Leesburg’s walkable scene features cafés, art galleries and boutique shops, while large-format retail and grocery centers are close at hand. Excellent access to healthcare: UF Health Leesburg Hospital serves the area and provides robust medical services locally. Outdoor recreation is abundant: nestled among the lakes of the Harris Chain, Leesburg offers parks, trails and lakeside activities minutes away for boating, fishing or lakeside sunsets. Why you’ll love it: Fully remodeled — you won’t need to lift a finger to move in. Great central location: quick access to major roads, shopping, dining, schools & healthcare. Attractive, durable finishes and smart layout—ideal for families, professionals or downsizers. A true blend of small-town Florida charm with convenient access to larger destinations. Don’t miss your chance to own a refreshed, stylish home in Leesburg’s thriving market. Schedule your tour today and imagine the ease and quality of life that await.

1008 Nebraska Street, Leesburg

$1,395,000

5 Beds ⋅ 4 Baths ⋅ N/A SubDv. ⋅ 34748 Zip Code

Welcome to your lakefront retreat designed for those who love to host, relax, and live life in style. Nestled on 1.66 acres along the shores of Lake Harris, part of Florida’s highly sought-after Chain of Lakes, this 4,420+ sq ft, 5-bedroom, 4-bath home exudes classic Florida charm. It provides comfort, thoughtful updates, and exceptional outdoor amenities for a resort-style estate. Enjoy 150 feet of direct waterfront with your private boathouse featuring a 418 sqft, upper-level guest apartment and balcony overlooking the lake, perfect for friends or weekend visitors. Spend your days boating, fishing, or exploring miles of scenic waterways, then unwind poolside or enjoy a twilight match on your private lighted tennis court. The outdoor experience is truly resort-caliber, highlighted by a sparkling pool surrounded by an entertainment deck and $90,000 in professional landscaping and lighting enhancements that elevate the property’s beauty day and night. Mature oaks, manicured grounds, and custom illumination create a warm, inviting ambiance ideal for gatherings and peaceful evenings by the water. Inside, the home exudes comfort and relaxation. The formal living area features a beautifully renovated stone fireplace, thoughtfully transformed from its original brick design to create a timeless focal point. The heart of the home, a spacious entertainer’s kitchen is perfectly designed for dinner parties and gatherings, with generous counter space, dual islands, quartz countertops, modern appliances, a large walk-in pantry and a seamless open layout connecting to multiple living and dining areas, this kitchen makes entertaining effortless and functional. With 5 bedrooms and 4 full baths, the home offers flexibility for family and guests. The primary bedroom is expansive with a large L-shaped walk-closet. Additional spaces include formal and casual living areas, a home office, and a flex room. The three-car garage provides abundant space for vehicles and storage. Located on a quiet dead-end street, the property offers privacy and tranquility while remaining just minutes from shopping, dining, and entertainment. Recent upgrades within the last five years include: $90,000 in Landscaping and lighting, two new HVAC systems, replaced well and sprinkler pumps, a well water treatment system, new outdoor privacy fence, rescreened pool deck, new hot water heaters in both the main home and boathouse, new boathouse roof with portable A/C, metal roof maintenance on the main home (screws and boots replaced), and fresh interior paint in multiple rooms. The kitchen has been extensively updated with a new refrigerator, dual oven, stovetop, sink, faucets, island countertop, and cabinet hardware—plus numerous additional improvements enhancing comfort, efficiency, and style. Live the ultimate Florida lifestyle—launch your boat from your private dock, take a refreshing swim, or host unforgettable gatherings under the stars. Nearby attractions include Mission Inn Resort & Club (championship golf, spa, and dining), Yalaha German Bakery & Beer Garden (a local favorite for brunch and live music), Lakeridge Winery (Central Florida’s premier vineyard and festival destination), Venetian Gardens Park (waterfront trails, marina, and community events), and The Villages, offering world-class shopping, dining, and nightly entertainment. Conveniently located minutes from the Florida Turnpike and 441, to all major attractions, and Orlando Airport(MCO)

4345 Corley Island Road, Leesburg

$299,000

5 Beds ⋅ 2 Baths ⋅ Leesburg Whispering Pines Annex SubDv. ⋅ 34748 Zip Code

Price Improvement! This beautifully renovated and spacious single-family home offers 2,108 sq ft of flexible living space with 4–5 bedrooms and 2 full baths. The inviting living room features a cozy fireplace and large doors overlooking the front yard. The updated kitchen includes stainless steel appliances, refreshed countertops, ample cabinetry, and extended space ideal for a coffee bar or buffet. The primary suite offers a sitting or office area, en-suite bath, and direct access to the laundry room and backyard. Situated on a large corner lot, this home also features a covered porch, an adjacent concrete patio, and a 10×17 powered workshop, perfect for storage, projects, or hobbies. Conveniently located near downtown Leesburg, parks, shopping, and dining. The seller may consider concessions.

1114 Oak Drive, Leesburg

$425,000

6 Beds ⋅ 6 Baths ⋅ Leesburg Sunshine Park SubDv. ⋅ 34748 Zip Code

Under contract-accepting backup offers. Located Just a few blocks from Downtown Leesburg (Beacon College, Restaurants, shopping), HWY 27 and 441, this 6 plex is fully occupied and income generating with management in place. There are 6, 1/1's along with 3 locking storage areas that could generate additional income. Rents are $800 (x2), $835, $900, $895, $901. The storage units are currently not rented. The units are all separately metered for power and share one water meter that the owner includes. Several tenants are long term (over 10 years). 4 of the 6 units have central A/C's and 2 utilize wall units. The roof was replaced in 2021 on both buildings. All units have 2 entrances and exits. Schedule an appointment with your agent today!

1120 Webster Street, Leesburg

$395,900

Leesburg SubDv. ⋅ 34748 Zip Code

Located in the heart of downtown Leesburg near the historic district. This well maintained 2-story property hosts two units. Each unit have separate front and rear entrance. 1st floor has a beautiful gathering room that features an electric fireplace, large closet and gives access to 2 private rooms. It also hosts a well-maintained kitchen that is recently upgraded and a full bath that is also upgraded. Close to the rear exit is the wash and dryer.2nd floor features a large living room, 3 bedrooms, eat-in kitchen, laundry closet and a full bathroom. Both units are fully remodeled with laminate floors, new appliances and freshly painted. Metal Roof 2024, 2nd floor AC 2025, 1st floor AC 2018 Great upside investment opportunity. Owner is a Real Estate Broker. 2nd Floor Photos taken prior to tenant occupancy 6 months ago.

1317 Main Street, Leesburg

$150,000

2 Beds ⋅ 1 Baths ⋅ N/A SubDv. ⋅ 34748 Zip Code

2144 Lisa Dare Dr, a charming 2-bedroom, 1-bath home nestled in Leesburg, FL. Offering 907 square feet of comfortable living space, "Zoning: RP" this property sits on a generous 0.5-acre lot, providing plenty of room for outdoor activities, gardening, or future possibilities. Inside, you’ll find a cozy layout perfect for everyday living, while outside the expansive yard offers both privacy and potential. Conveniently located near local shopping, dining, this home is a wonderful opportunity for first-time buyers, downsizers, or anyone seeking a peaceful Florida lifestyle.Note: buyers I emphasize the importance of conducting thorough due diligence to ensure that the property meets your expectations and requirements.

2144 Lisa Dare Drive, Leesburg

$395,000

3 Beds ⋅ 2 Baths ⋅ Leesburg Beverly Shores SubDv. ⋅ 34748 Zip Code

Beautiful ranch home situated on a corner, double lot on Leesburg's Beverly Shores. A quiet natural setting with access to the Chain of Lakes and just a block away from water access, docks and fishing. Just minutes to downtown Leesburg and parks. The quality of this well maintained home will catch your attention! The brick exterior is solid and in excellent condition and terrazzo flooring. House has a life time rhino covering and windows and screens have a lifetime warranty. There is a side room that could be converted to a bedroom or potential "mother-in-law" suit. Several renovations have been done including the roof and windows replaced in 2017; AC replaced in 2012 & newer flooring throughout. The spacious floor plan is great for entertaining and has a separate office/storage room with private entrance which could be converted to an additional bedroom. The oversized, finished garage is great for storage and parking but could be great to turn into a home gym or ever turn into additional living space. An additional carport is built off of the house as well. This is a great place to call “home” scheduled your showing today.

803 N Shore Drive, Leesburg

$1,150,000

3 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 34748 Zip Code

9-acre LAKEFRONT DREAM HOME ON LAKE GRIFFIN with NEW CUSTOM SCREENED IN $250K BOATHOUSE with high-end kitchen and grill! Plus bonus WORKSHOP/fish house with garage on the property. This beautiful 3 bedroom 3.5 bath home offers 3,200 sqft. The property stands majestically on an expansive 9-acre lot with a vast lawn that gently slops towards the pristine shores of Lake Griffin. The architecture of the house perfectly captures the essence of LAKESIDE LIVING, with large sliding doors/ windows that provide breathtaking views of the shimmering waters and draw in an abundance of natural light. Lake Griffin is one of the most pristine lakes amount he CHAIN OF LAKES in Florida. the beautiful body of water stretches over 9,400 acres and offers a serene and picturesque setting for water enthusiast and nature lovers alike. As you walk inside, the hardwood floors in the foyer exude warmth and elegance, seamlessly blending with the soothing color palette that mirrors the tranquil blues and greens of the lake.The FRENCH DOORS will bring you to the living area. The OPEN-CONCEPT all-tile layout enhances the flow of the home, creating a sense of cohesion between the living area with gas FIREPLACE, Formal dining room, and spacious gourmet kitchen, equipped with top-of-the-line STAINLESS STEEL appliances, wood cabinets, GRANITE COUNTERS, and a large bar. It was evident that no expense was spared in creating a space that combines functionality and beauty for even the most discerning culinary enthusiast. Right next to the kitchen, you will find a 9 X 32 SUNROOM which is a perfect space for entertaining along with a recently renovated hallway with a BAR. The primary bedroom off the foyer exudes relaxation and comfort. Large WALK-in CLOSET. The windows provide panoramic views of the lake, while the en-suite bathroom boasts a spa-like atmosphere complete with a deep soaking TUB, DUAL vanities, and a separate shower. All Bedrooms have their own private bathroom. An Extra 4th bedroom can be built upstairs in the unfinished ATTIC Space. Beautiful SCREENED In 47 X 14 LANAI where you can enjoy entertaining family and friends or relaxing on the lounge chairs looking at the incredible picturesque backyard with lakefront views. The Owners went all out in making this the perfect lake house by adding a $250k custom BOAT DOCK with jet sky launch and SCREENED in KITCHEN with BBQ GRILL, SINK, and FRIDGE. A BREATHTAKING LOUNGE area to enjoy the SUNSET and incredible view of the LAKE. Take your boat out and enjoy BASS fishing or boating around the chain of lakes, visiting Mt Dora and surrounding areas. The home has a 2 car carport but there is an additional detached garage/FISH HOUSE WORKSHOP along with a covered 3 carport for extra vehicles/trailers for a total of 6 spaces. This waterfront home on Lake Griffin is truly a gem in the Chain of Lakes. Its elevated design, attention to detail, and luxurious amenities make it an ideal retreat for those seeking a truly exceptional lakeside living experience with NO HOA. It was apparent that the owners had masterfully curated this space, ensuring that every waking moment in this luxury haven was one of serenity and rejuvenation. There are 3 parcels included in this sale and can be split if desired. This property is currently a very sucessful short term rental.

416 Hancock Road, Leesburg

$799,900

4 Beds ⋅ 4 Baths ⋅ Silver Lake Estates SubDv. ⋅ 34788 Zip Code

Under contract-accepting backup offers. Virtually Staged. Silver Lake Waterfront Estate – First Time Ever Offered! This extraordinary Silver Lake waterfront estate is being offered for the first time and presents a rare opportunity to own a true legacy property. Nestled on 2.15 acres with 177 feet of pristine lake frontage, the property includes a spacious two-story main residence with over 4,985 square feet of living space, as well as a detached 700 sq ft guest house with multiple hobby and workshop rooms. The main home features 4 bedrooms and 3.5 baths, with elegant formal living and dining rooms showcasing hardwood floors, built-in shelving, and a wood-burning fireplace. At the heart of the home is a beautifully designed kitchen offering granite countertops, abundant cabinetry, a gas range, double ovens, pantry, and convenient pass-throughs to both the sunroom and family room. Adjacent to the kitchen is a large tiled breakfast area and family room with French doors leading to the side yard, along with a 33x11 sunroom filled with windows and French doors opening to the backyard paver patio. Also on the main level is an 11x9 den/office with rich wood accents, a spacious 20x19 game room with private entry from the carport, a welcoming foyer, and a powder room for guests. Upstairs features brand-new carpet installed in 2025 and two master suites. The primary suite boasts stunning lake views, 2 walk-in closets, a double vanity, and a tiled walk-in shower. The second master suite offers a wall-to-wall closet and private bath with walk-in shower. The third bedroom includes wall-to-wall closets and sliding doors, while the 3rd full bath features double vanities, a pocket door separating the water closet, and a tiled tub/shower combo. A large laundry room with built-in ironing board, cabinet storage, and folding counter completes the interior layout. Recent updates include a new roof in 2024, attic insulation added in 2023, new ductwork and under-house insulation in 2022, two HVAC units (replaced in 2007), two gas water heaters (one replaced in 2016), all new windows, new drainfield installed in 2012, new well in 2020, along with tank in 2017 and new sprinkler pump in 2020. Outdoor living is elevated by a 20x19 screened paver veranda with vaulted ceilings and an atrium water feature, a 19x19 covered carport with storage closets, and a 32x29 open brick paver patio in the backyard. The detached guest house offers 700 sq ft of living space with a full tiled bath and walk-in shower, a 13x10 hobby room with built-in desk and drawers, a 20x10 workshop with adjoining 13x9 darkroom perfect for hobbies or creative space, and a 13x9 well room housing the water softener. The guest house also features a new roof in 2024, HVAC from 2008, and was replumbed in 2022. The entire estate is beautifully landscaped with majestic oaks, and includes a full irrigation system with pump replaced in 2020. The living square footage includes the guest house. This Silver Lake estate is a rare find offering unparalleled space, comfort, and views—schedule your private tour today.

9223 Silver Lake Drive, Leesburg

$950,000

34788 Zip Code

Under contract-accepting backup offers. DEVELOPER ALERT: This Mixed Use property spans 17.14 acres, with 6 acres available for a PLANNED UNIT DEVELOPMENT (PUD) capable of accommodating 27 residential units. While the owner is looking for outright sale he is open to a PARTNERSHIP OR JOINT VENTURE with experienced suitable developer, making it an attractive opportunity for investors or developers. Prime area next to Mall, restaurants and leesburg Airport. Recent enviromental has been completed and is attached along with survey. (The value is in the land)

32900 Radio Road, Leesburg

$449,850

34748 Zip Code

Great corner location with 145 ft of frontage on busy SR 44 (South Street) in The City of Leesburg. Property is currently zoned R2 and located around commercial and residential properties. There is currently a business located on this property in which the owner resides. The main building has 2379 sq ft of heated & cooled space with 2 bedrooms & 2 baths, full kitchen, multiple offices, showroom and work area. 2nd building is a 1925 sq ft warehouse/workshop with 2 overhead doors. Over 1/2 acre with plenty of parking.

2405 South Street, Leesburg

$1,000,000

24 Beds ⋅ 12 Baths ⋅ Leesburg Lees SubDv. ⋅ 34748 Zip Code

Under contract-accepting backup offers. Unlock incredible potential with this 12-unit apartment building, perfect for the savvy investor seeking to gain equity and add value. Ten of the units have already been beautifully gutted and renovated, while one is currently being updated and another is in the process of electrical improvements. Located in a prime area near the stunning chain of lakes and vibrant downtown Leesburg, this property offers the ideal blend of convenience and appeal. Don’t miss your chance to capitalize on this lucrative investment! Seller is selling his 112 unit rental portfolio properties including 1000 E CAROLINE STREET, TAVARES, Florida 32778, 737 ALBROOK STREET, MASCOTTE, Florida 34753, 617 E MYERS BOULEVARD, MASCOTTE, Florida 34753, 30 WAFFORD STREET, UMATILLA, Florida 32784, 15992 W COLONIAL DRIVE, OAKLAND, Florida 34787, and 301 S EAST STREET, LEESBURG, Florida 34748.

301 S East Street, Leesburg

$224,500

4 Beds ⋅ 3 Baths ⋅ Leesburg Lsbg Realty Cos Add SubDv. ⋅ 34748 Zip Code

Welcome to your dream home! This stunning 4-bedroom, 3-bathroom residence boasts a bright and inviting living/dining room combo, perfect for entertaining or gatherings. The kitchen features elegant granite countertops and modern stainless steel appliances, making it a chef's delight. Step outside to discover a spacious backyard, ideal for outdoor activities or relaxing in the sun. With its perfect blend of comfort and style, this home is a must-see! Corporate seller, selling as/is, may not know age of roof, ac, systems.

112 S Moss Street, Leesburg

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