Leesburg Condos For Sale - 8 condos

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: Wake up every morning to breathtaking views and sunrises over Lake Griffin from your screened front porch and from many rooms throughout the home. This move-in ready residence offers the perfect blend of comfort, style, and low-maintenance living. The driveway leads you to this unique single-family duplex-style home with the rare bonus of an oversized two-car garage with laundry area. Inside, the home feels light and open with a cathedral ceiling great room featuring a gas fireplace with quartz surround, perfect for cozy evenings. The updated kitchen is designed for both everyday living and entertaining, featuring quartz counter tops, shaker-style cabinetry, stainless steel appliances, a WiFi-enabled range and refrigerator, in-cabinet microwave drawer, and abundant storage. LED recessed and under-cabinet lighting brighten the space beautifully. The private master suite features a vaulted ceiling, oversized walk-in closet, and a fully updated spa-style bath with dual walk-in showers, double sinks, and granite countertops. The split-bedroom floor plan provides privacy, with two additional spacious bedrooms filled with natural light and sharing a guest bath with double vanity and granite counters. Simply relax on your porch, enjoy the panoramic lake views, and let someone else handle the maintenance. Low-stress living, incredible views, and a beautifully updated home — all in one perfect package.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Christopher Cheshire (352-446-6174)

Remarks: WITH GARAGE + BONUS SPACE! This home offers more than most condos in this price range, including a private garage, additional living space, and access to water amenities. This well-maintained 2-bedroom, 2-bath condominium offers exceptional versatility with a spacious bonus room that was formerly a lanai and has been thoughtfully converted and equipped with a mini-split system for year-round comfort. The generous size of this space allows the option to create an additional room or office while still maintaining a large bonus or gathering area—ideal for today’s lifestyle needs. Residents enjoy access to a sparkling community pool and a private boat dock with first-come, first-served slips, perfect for embracing the waterfront lifestyle. Golf cart access to historic downtown Leesburg places shopping, dining, festivals, and waterfront events just minutes away. Inside, the home features direct access from the attached one-car garage, which includes attic access to an expansive storage area above—an uncommon and valuable feature. The split-bedroom floor plan provides privacy, with a guest bedroom and full bathroom conveniently located near the front of the home. The open-concept living and dining area is filled with natural light and enhanced by vaulted ceilings, creating an inviting space for everyday living or entertaining. The kitchen flows seamlessly into the main living area, while the primary suite offers a walk-in closet and a private en-suite bath for comfortable, low-maintenance living. With flexible living spaces, abundant storage, and an unbeatable location in one of Leesburg’s most sought-after communities, this home presents a rare opportunity to enjoy the best of Florida condominium living. Schedule your private showing today.

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

Listing Agent: Misty Noland (352-255-2502)

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! Motivated Seller – Your Dream Home Awaits! Get ready to fall in love with a community that truly has it all! Enjoy a heated indoor Olympic-size swimming pool, a sparkling outdoor pool, two welcoming community centers, and a lively calendar full of fun activities and events. Whether you're staying active or meeting new friends, there’s always something exciting happening! Sports enthusiasts will love the tennis courts, pickleball courts, bocce ball, and shuffleboard—perfect for friendly competition and sunny afternoons. Ideally located near two major hospitals, fantastic shopping, delicious restaurants, and charming towns like Mount Dora and The Villages, you’re perfectly positioned to enjoy both convenience and a peaceful retreat. This beautiful home offers gorgeous views from every room and a lifestyle that’s truly hard to beat. With a recent price reduction and a motivated seller ready to make a deal, now is the perfect time to say YES to your next chapter. Come see it today and start living the life you deserve!

Listing is courtesy of: GREAT EXPECTATIONS REALTY, LLC (352-817-9160)

Listing Agent: Lori Anderson (954-296-9836)

Remarks: Under contract-accepting backup offers. BIG price reduction! The previous Cash Buyer wasn't approved by HOA on credit so this is somebody's lucky day!!!! Scottish Highlands 55+ community. Vacant and move-in ready! No Bond and beautifully updated throughout. Recent upgrades include a new roof, new A/C, laminate flooring, stainless steel appliances, granite countertops, newer soft-close cabinets, and a gas range. Home also features a painted/finished driveway and front porch, garage screen door, and retractable front entry screen. The two-car garage includes a window A/C unit and has been partially set up as a workshop, while still providing space to park a car and a golf cart. The backyard is beautifully landscaped and private, perfect for relaxing or entertaining. This well-maintained home is fully updated and ready for immediate occupancy.

Listing is courtesy of: BLU SEA DREAMS,LLC (352-915-5100)

Listing Agent: Elizabeth Fox (352-915-5100)

Remarks: Discover one of the largest and most desirable models in Scottish Highlands, a sought-after Pringle 55+ active adult community in Leesburg. This spacious 3-bedroom, 2-bath home offers an inviting layout featuring a generous living room seamlessly combined with a formal dining area, plus a bright and airy Florida room perfect for relaxing or entertaining. The split-bedroom floor plan provides privacy, while the oversized indoor laundry room adds everyday convenience. The expansive primary suite is a true retreat, complete with a large walk-in closet and an en-suite bath featuring dual sinks, a separate tub, and a walk-in shower. Step out to the screened porch off the Florida room and enjoy peaceful views of a community pond and nearby tennis courts. Ideally located just moments from the clubhouse, indoor and outdoor pools, fitness and recreation facilities, and courts for tennis and pickleball, this golf cart-friendly community also offers a full calendar of social events. With easy access to shopping and the vibrant Golden Triangle areas of Mount Dora, Tavares, and Eustis—known for their charming downtowns, local dining, and year-round festivals—this home truly has it all. Schedule your private showing today!

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (352-729-6528)

Listing Agent: Betty Hensinger (352-267-5028)

Remarks: Check out this 3 bed, 2 bath Condo in the charming 55+ community of Chesterbrook, this is just minutes from Lady Lake, The Villages, and scenic Lake Griffin, part of the renowned Chain of Lakes! This ground-floor condominium features a spacious open floor plan designed for modern living. Step inside this beautiful home that features brand-new luxury vinyl flooring throughout the expansive living areas, and updated kitchen! Enjoy the convenience of direct ground-floor access with dedicated parking just steps from your door. The enclosed patio offers a perfect retreat on hot summer days, providing a comfortable indoor-outdoor space to relax in privacy. Chesterbrook boasts fantastic amenities, including a refreshing pool, a welcoming clubhouse, a bathhouse, and shuffleboard courts. With easy access to a variety of local dining options, and just a short 15-minute drive to The Villages, you’ll find everything within reach. The condo fee covers essential services such as garbage, water, sewer, and meticulous grounds maintenance, making for truly effortless living. If you’re searching for a stylish and comfortable place to call home, no need to look any further!

Listing is courtesy of: ISLAND REAL EST&PROP MGMT INC (727-804-7719)

Listing Agent: Erik Parks (727-804-7719)