Remarks: NEW LOW PRICE!!!! — a quiet, well-kept 55+ community just minutes from downtown Leesburg, 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. RETIRE YOUR LAWN MOWER 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: Freshly updated and ideally located in the heart of downtown Leesburg, this 2-bedroom, 2-bath second-floor end-unit condo offers an affordable opportunity for easy everyday living, a smart alternative to renting, or a practical addition to an investment portfolio. Move-in ready with fresh interior paint, no popcorn ceilings, durable tile and luxury vinyl plank flooring, and new remote-control ceiling fans with LED lighting in the living room and both bedrooms, the home has a clean, modern feel without the upkeep of carpet. The kitchen is well equipped with granite countertops, ample cabinetry, and comfortable functionality for daily use. Added conveniences include water and sewer included in the HOA, a private assigned covered parking space, and onsite laundry facilities. The downtown Leesburg location places you near local dining, shopping, events, schools, medical offices, and commuter routes, offering the walkability and convenience buyers are looking for. With strong affordability and rental potential, this condo is a versatile choice for an owner-occupant or investor. Schedule your private showing today.

Listing is courtesy of: VANGIE BERRY SIGNATURE REALTY (352-742-7355)

Listing Agent: Angela Phillips (240-462-0646)

Remarks: Under contract-accepting backup offers. LOWEST PRICED 2Bed/2Bath with GARAGE & SUNROOM in Leesburg!! Price recently reduced by $12,500 -- Seller motivated! Welcome home to 100 E. Oak Terrace Dr., Unit B2 -- FIRST FLOOR Condo. Freshly painted throughout, tankless water heater, Laundry is conveniently located inside the unit with Washer/Dryer Included!. Enjoy your morning coffee on the enclosed Sunroom featuring stone tile with wood accent ceiling, and is wired for a TV. This lovely residence offers 1518 SqFt unit under AC, open layout, laminate flooring throughout, NO CARPET. Some flooring needs repair/replacing in the Kitchen and Living Room due to recent foundation repairs, SELLER is now offering a credit towards flooring. This building recently underwent foundation stabilization with a LIFETIME GUARANTEE giving you peace of mind. Your private Primary Bedroom features a walk-in closet, ensuite bathroom with tub/shower combo and single vanity. Previous owner updated and expanded BOTH BATHROOMS, so these bathrooms are larger than most units. Guest bathroom is easily accessible, offers a tiled walk-in shower with glass sliding doors. The Condo building has its own separate semi-private entrance with a new Intercom Camera System that gives access to ONLY you and 3 other neighbors. YOUR PRIVATE GARAGE offers a pebble finish flooring, wood accent ceiling, plus tall solid wood cabinets for storage. Be sure to check out the floor plan in the photos. The Condo is located less than a mile away from Downtown Entertainment District Leesburg, Venetian Gardens and just a ride away from The Villages, Mount Dora, Tavares and/or Orlando. This Condominium is just at the perfect location for those looking to be tucked in from the busy roads, the entrance of the complex is at the dead end of Oak Terrace Dr. This peaceful and serene community backs up to 88 Acres of natural beauty of Bourlay Historic Nature Park. You can either walk or bike the trails and enjoy the beautiful views of Lake Griffin. CALL FOR YOUR PRIVATE SHOWING! THIS is the Best Priced condo in Leesburg with a garage and is available for a quick sale!

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

Listing Agent: Rachel Rivera (407-230-0235)

Remarks: Move-in ready! This beautifully updated first-floor condo offers comfort, convenience, and low-maintenance living all in one. Freshly painted throughout, the interior feels clean and inviting from the moment you step inside. The kitchen features brand-new stainless steel appliances, providing a modern touch for everyday cooking and entertaining. Enjoy the convenience of an in-unit laundry closet complete with full size washer and dryer included, plus the added bonus of a private one-car garage for extra storage and parking There is a private attic over the garage. Sliding glass doors off the dining room fill the living space with natural light and lead out to a peaceful screened-in lanai. The perfect spot to enjoy your morning coffee or unwind in the evening without worrying about bugs or weather. Whether you’re looking for a seasonal retreat, investment opportunity, or full-time residence, this charming condo checks all the boxes with its ideal first-floor location and thoughtful updates throughout.

Listing is courtesy of: COLDWELL BANKER VANGUARD LIFESTYLE REALTY (352-648-0096)

Listing Agent: Bethany Burge Bosbous (352-223-9500)

Remarks: Discover elegance and ease in this beautifully remodeled 2-bedroom, 2-bath condo, tucked away in the premier 55+ community of Chesterbrook. Glowing with natural warmth, the spacious open-concept layout effortlessly connects the living and dining area to a serene enclosed porch, the perfect spot for your morning coffee. A bonus is additional storage in the attic space located on the enclosed porch, so nice to have that space you will not find on the 1st floor. High-end finishes elevate every corner, featuring Venatino Italian tile, durable laminate flooring, granite countertops, and custom maple cabinetry. Both bathrooms have been stunningly upgraded with Mirasol glazed ceramic wall tiles, including a luxurious jacuzzi jetted tub in the guest bath. Retreat to the generous primary suite, which easily accommodates a king-size bed and boasts an impressive, oversized walk-in closet. The large second bedroom offers fantastic flexibility, making it an ideal space for guests, a home office, or a hobby room. Outside, Chesterbrook’s sparkling community pool is ready for summer relaxation. Perfectly positioned, you are just minutes from Lady Lake, The Villages, and Lake Griffin. Your stylish, low-maintenance retreat awaits, in addition to the remodel, please note excellent mechanical updates: a BRAND NEW ROOF (February 2026) and AC (2020).

Listing is courtesy of: GARRISON REALTY GROUP LLC (352-901-3415)

Listing Agent: Jennifer Garrison (352-805-5550)

Remarks: New Roof!! Welcome to this cozy and well-maintained 2-bedroom, 2-bath condo located in a 55+ community. This second-floor unit features a private entry, convenient parking, and no neighbors above for added privacy. The interior has been freshly painted and includes an enclosed porch a perfect for relaxing and enjoying the Florida lifestyle. Chesterbrook Condo offers excellent amenities, including a clubhouse, community pool, and shuffleboard. The HOA covers water, sewer, garbage, and cable, making for easy, low-maintenance living. Centrally located near shopping, dining, entertainment, and medical facilities, with a bus stop conveniently located within the community for easy access to daily needs. Enjoy!

Listing is courtesy of: PROFESSIONAL REAL ESTATE TEAM (407-483-4964)

Listing Agent: Diana Perez (407-483-4964)

Remarks: FEEL RIGHT AT HOME IN THIS WARM & INVITING 2-BEDROOM GEM IN A FRIENDLY 55+ COMMUNITY! Situated on a peaceful street, this cozy home offers a comfortable layout with 2 full bathrooms and a flexible bonus room that can be your office, hobby room, or reading space. The interior feels bright, clean, and easy to maintain - perfect for relaxed living. The home comes fully furnished, making your move simple and stress-free. The roof was replaced in 2007 and has been well maintained. Mature landscaping and an extra-wide driveway add everyday convenience and charm. Nestled among beautiful mature trees, the community offers a peaceful Florida lifestyle with resort-style amenities just steps away, including an indoor Olympic-size heated pool, outdoor pool, tennis and pickleball courts, a fitness center, RV/Boat storage (check availability), and a lively clubhouse with frequent social activities. It’s a welcoming environment where it’s easy to make new friends and stay active. You’re also in a fantastic location - right in Lake County’s Golden Triangle, just minutes from Mount Dora, Eustis, and Tavares, known for their festivals, waterfront dining, and charming historic downtowns. Enjoy quick access to the Harris Chain of Lakes, and you're only about 30 miles from Orlando and an easy drive to Daytona Beach and New Smyrna Beach. HOA includes cable and internet, making this an ideal option for snowbirds or full-time residents who love walking, swimming, and enjoying the Florida sunshine.

Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)

Listing Agent: Vildan Nigro (352-988-3824)

Remarks: Welcome to Pennbrooke Fairways, a sought-after gated golf community in Leesburg! This well-maintained condominium at 420 Glen Arbor Lane offers comfortable, low-maintenance living with access to an impressive array of community amenities. Inside, you’ll find a bright and inviting floor plan designed for both everyday living and entertaining. Enjoy a spacious living area, well-appointed kitchen, and comfortable bedrooms, along with a private outdoor space perfect for relaxing with your morning coffee or evening beverage. Pennbrooke Fairways residents enjoy access to golf courses, swimming pools, fitness facilities, tennis and pickleball courts, clubhouse activities, and a vibrant social calendar. Conveniently located near shopping, dining, medical facilities, and major roadways, this home provides the perfect blend of comfort, convenience, and active Florida living. Schedule your private showing today and discover everything this wonderful community has to offer!

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Taylor Oaks (352-459-9720)

Remarks: ***Seller offering $5,000 in concession*** The open-concept living area seamlessly connects the living room, dining area, and stunning kitchen. The kitchen is an entertainer's dream, boasting stainless steel appliances that add a modern touch. With ample cabinet space, the kitchen provides both functionality and style, making meal preparation a delightful experience. Step into the spacious master bedroom with a spacious walk-in closet and private bathroom. The condo also offers a second well-proportioned bedroom, perfect for guests or a home office, providing versatility to suit your lifestyle. The two bathrooms are tastefully designed, combining practicality with a touch of luxury. The home also features a brand new water heater. One of the standout features of this condo are the screened in patio and the attached one-car garage, providing secure parking and additional storage space. Each condo comes with additional storage space in the attic located on the second floor. Seller Offering $5,000 in Concessions! Use it toward your closing costs, down payment, or even a rate buy-down to help make homeownership more affordable. Don’t miss this opportunity — schedule your showing today!

Listing is courtesy of: OLIVER MOSLEY REALTY INC (407-495-2794)

Listing Agent: Shelly Osborne Llc (407-319-4053)