Displaying: For Sale
Location: Leesburg
Property Type(s): Condos
Living Area Square Feet: 1000 to 1499
Do Not Show Listings
Leesburg - 7 properties found
1 DURNESS CT #1, LEESBURG, FL 34788
$183,000100 Days on yellowkey MLS ID: OM717358
REDUCED by $2,000 (1.1%) on 04/30/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1200 Built: 1988 Tax: $1,389 (2025)Community: Scottish Highlands Condo Ph BCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,389
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Price Reduced! Motivated Seller – Your Dream Home Awaits! Come experience a warm, welcoming community where neighbors become friends and there’s always something to enjoy. From the heated indoor Olympic-size pool to the sparkling outdoor pool, two inviting community centers, and a full calendar of social events, you’ll love how easy it is to stay active, connected, and entertained. If you enjoy the outdoors and a little friendly competition, you’ll appreciate the tennis courts, pickleball, bocce ball, and shuffleboard—perfect for relaxing afternoons and making new friends. Located near two major hospitals, great shopping, delicious restaurants, and charming destinations like Mount Dora and The Villages, you’re right where you want to be—close to everything, yet tucked into a peaceful setting. This beautiful single-family residence (SFR) is designed for comfortable, easy living with all ceramic tile flooring throughout—perfect for low-maintenance living and a clean, modern feel. Natural light fills the home, and the views from every room create a bright and inviting atmosphere you’ll love coming home to. With a recent price reduction and a motivated seller, this is your opportunity to step into a lifestyle that’s as enjoyable as it is effortless. Come see it for yourself—you may just find exactly what you’ve been looking for.
Listing is courtesy of: GREAT EXPECTATIONS REALTY, LLC (352-817-9160)
Listing Agent: Lori Anderson (954-296-9836)
500 NEWELL HILL RD #101A, LEESBURG, FL 34748
$68,00068 Days on yellowkey MLS ID: G5108494
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1975 Tax: $1,041 (2025)Community: Leesburg Chesterbrook CondoCondo
Taxes:$1,041
Elementary School: Beverly Shores Elem
High School: Leesburg High
Middle School: Oak Park Middle
Remarks: RETIRE THE LAWN TOOLS AND WEEDWHACKERS!!! — 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. 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)
500 NEWELL HILL RD #108B, LEESBURG, FL 34748
$69,90088 Days on yellowkey MLS ID: W7882615
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1413 Built: 1980Monthly Fee: $645 Tax: $1,161 (2025)Community: Leesburg Chesterbrook 02 CondoCondo
Taxes:$1,161
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)
500 NEWELL HILL RD #108A, LEESBURG, FL 34748
$89,000271 Days on yellowkey MLS ID: G5100448
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1413 Built: 1980Monthly Fee: $645 Tax: $1,273 (2024)Community: Leesburg Chesterbrook 02 CondoSpa: NoCondo
Taxes:$1,273
Tax Year: 2024
Remarks: This 3/2 condo in the 55+ community of Chesterbrook is looking for a new owner. This community is close to everything Leesburg has to offer, restaurants, health care facilities, mall, auto dealers and 20 minutes from the Villages. The unit has a large primary bedroom with ensuite bath and dual sinks. Sit out in the morning on the porch. Call for your appointment today. Community has completed the new roofs and unit has been freshly painted.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Nicky Lerch (571-212-2077)
916 BELLE OAK DR, LEESBURG, FL 34748
$235,00088 Days on yellowkey MLS ID: G5107739
REDUCED by $10,000 (4.1%) on 03/31/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1306 Built: 1985 Tax: $1,478 (2025)Community: Leesburg Oaks Leesburg Condo Ph 01Condo
Taxes:$1,478
Remarks: One of the most spacious and versatile condos with garage + water access! This well-maintained 2-bedroom, 2-bath home offers a rare combination of features not typically found in this price range, including a private attached garage, expansive bonus living space, and access to waterfront amenities. With approximately 1,306 sq ft of heated living area and a thoughtfully designed layout, this home provides both comfort and flexibility for a variety of lifestyles. The open-concept main living area is enhanced by vaulted ceilings and abundant natural light, creating a bright and inviting space that flows seamlessly between the living and dining areas. The kitchen is both functional and well-appointed, offering ample cabinetry, generous counter space, and easy connection to the main living areas—ideal for everyday living and entertaining. A standout feature of this home is the oversized 31x14 bonus room, formerly a lanai and now fully enclosed and equipped with a mini-split system for year-round comfort. This additional space significantly expands the home’s usability and can serve as a second living area, home office, fitness room, or even be reconfigured to create additional sleeping space while still maintaining a large gathering area—an uncommon and valuable feature in condominium living. The split-bedroom floor plan provides privacy, with a comfortable guest bedroom and full bathroom located toward the front of the home, while the primary suite is positioned for a more private retreat. The primary bedroom offers generous space, a walk-in closet, and an en-suite bath featuring dual sinks and a walk-in shower. Additional highlights include direct access from the attached one-car garage, along with attic access providing substantial storage space—another rare benefit in this type of property. Residents enjoy access to a community pool as well as a private boat dock with first-come, first-served slips, offering the opportunity to enjoy boating, fishing, and waterfront living. Golf cart access to historic downtown Leesburg places shopping, dining, festivals, and waterfront events just minutes away, enhancing both convenience and lifestyle. With its unique combination of expanded living space, private garage, abundant storage, and access to water and community amenities, this home stands out from other condominiums in the area. Whether you are seeking low-maintenance living with added flexibility or a property that offers more space and features than typically available at this price point, this is a rare opportunity in one of Leesburg’s most desirable communities. Schedule your private showing today.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-735-4433)
Listing Agent: Misty Noland (352-255-2502)
500 NEWELL HILL RD #106D, LEESBURG, FL 34748
$60,000132 Days on yellowkey MLS ID: S5140606
REDUCED by $10,000 (14.3%) on 04/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1979Monthly Fee: $870 Tax: $1,049 (2025)Community: Chesterbrook 2 CondoCondo
Taxes:$1,049
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)
2215 ORKNEY DR, LEESBURG, FL 34788
$204,900150 Days on yellowkey MLS ID: G5104796
1 Days Off yellowkey (back on 3/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1304 Built: 1989Monthly Fee: $215 Tax: $1,383 (2025)Community: Scottish Highlands Condo Ph VCondo
Taxes:$1,383
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)
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