Timberwoods Estates Homes with Tennis Court(s) Community Features

Timberwoods Estates Homes with Tennis Court(s) Community Features

Welcome to Timberwoods Estates, an enchanting community nestled in the heart of Wildwood, Florida, within the picturesque Sumter County. This charming subdivision offers a perfect blend of tranquility and active living, making it an ideal haven for families, retirees, and everyone in between.

Timberwoods Estates is renowned for its inviting atmosphere and beautifully designed homes, many of which feature modern amenities and spacious layouts that cater to a variety of lifestyles. One of the standout features of this community is its exclusive access to tennis courts, allowing residents to engage in friendly matches and enjoy an active lifestyle right at their doorstep. Whether you’re a seasoned player or a beginner looking to learn, the tennis courts provide a wonderful opportunity to socialize and stay fit.

In addition to tennis, Timberwoods Estates boasts a variety of community features that enhance the living experience. Residents can take leisurely strolls along tree-lined streets, enjoy picnics in well-maintained parks, or participate in community events that foster a strong sense of camaraderie. The community is also conveniently located near shopping, dining, and recreational activities, ensuring that everything you need is just a short drive away.

With its prime location in Wildwood and a vibrant community spirit, Timberwoods Estates is not just a place to live; it’s a lifestyle. Discover the charm of this remarkable subdivision and explore the homes that await you in this delightful tennis-friendly enclave. Your dream home in Timberwoods Estates is just around the corner!

Newest Timberwoods Estates Homes with Tennis Court(s) Community Features

$124,900
2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
Start enjoying the Florida lifestyle in this inviting 2-bedroom, 2-bath home designed for comfortable, low-maintenance living. The open floor plan creates a bright and welcoming space that's perfect for entertaining friends or simply relaxing at home. One of the home's standout features is the spacious screened front lanai—the ideal spot to enjoy your morning coffee, visit with neighbors, or unwind while taking in Florida's beautiful weather year-round. The kitchen is thoughtfully designed to maximize efficiency, offering everything you need within easy reach while remaining open to the living and dining areas, so you're always part of the conversation when entertaining. Both bedrooms are comfortably sized, providing plenty of room for overnight guests, hobbies, or a home office. Two full bathrooms add convenience and privacy for you and your visitors. Outside, you'll find a large carport with ample parking and a generously sized storage shed with direct access to the laundry room. The extra storage space is perfect for tools, seasonal decorations, golf gear, bicycles, or all the extras that make Florida living so enjoyable. Whether you're searching for a full-time residence or a seasonal getaway, this home offers the comfort, convenience, and easygoing lifestyle you've been looking for. Just move in, relax, and start enjoying everything your Florida retirement community has to give. The community is absolutely gorgeous with countless amenities, which include: large swimming pool with hot tub, 18 hole championship golf course, driving range and putting greens, shuffleboard, tennis, pickle ball, fitness center, library, billiards room, softball field, and a 5 star restaurant and lounge. What more can you ask for? This is a beautiful home in a beautiful community. You won't be disappointed!!!

413 S Timber Trail, Wildwood
$89,900
2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
Nestled in the beautiful and activity-rich Continental Country Club, this AWESOME 2-bedroom, 2-bath home offers an open, spacious floor plan and an unbeatable location near the back gate for quick access to Hwy 44, 175, the Turnpike, The Villages, shopping, dining, and more. Inside, you'll find exceptional storage throughout with abundant cabinets, countertops, and closets-including an impressive four closets in the primary bedroom-along with roomy, well-laid-out bathrooms ready for your personal touch. The home features convenient inside laundry, a welcoming front sidewalk, a bight Florida room, covered carport, and a large storage shed perfect for tools, hobbies, or golf gear. This property is priced right and presents a fantastic opportunity to bring your updating ideas and make it truly yours. A Resident owner Certificate conveys with the home, providing lower HOA fees and full access to Continental's outstanding amenities including a resort-style pool, fitness center, clubhouse, fishing, crafts, woodworking, softball, golf, and countless activities designed for an active Florida lifestyle.

103 N Timber Trail, Wildwood
$128,500
2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
- This fabulous 2-bedroom, 2-bath home is truly ready for you, beautifully updated and tastefully remodeled to give you the most comfort, style, and easy Florida living. Inside, you’ll find abundant storage, generous cabinetry, Walkin closets, and a flowing floor plan that makes the home feel open and inviting from the moment you step in. The charming front screen room is perfect for morning coffee or evening relaxation, and the home sits proudly on a huge corner lot near the back gate—giving you quick, convenient access to The Village of Fenney, Sawgrass, Middleton, Chitty Chatty, Brownwood Square, the new Super Walmart, and so many other local attractions. This home is nestled in a very active gated golf community offering endless activities, beautiful nature walks, fishing, swimming, and plenty of fun at the popular Oaks Restaurant and Lounge. Continental Country Club is truly wonderful place to enjoy time with family and friends and to embrace your retirement in beautiful, sunny Florida—come experience the lifestyle and make this home yours!! (more pictures to come)

101 Cypress Road, Wildwood
$159,000
2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
PRICE DROP! BEAUTIFULLY RENOVATED HOME ON LAND NEAR THE VILLAGES! Welcome to this fully updated 2-bedroom, 2-bath home offering modern comfort, stylish finishes, and an unbeatable location just minutes from The Villages. Completely refreshed throughout, this move-in-ready property features a bright and inviting floor plan with all-new interior updates, fresh finishes, and brand-new appliances included. The spacious kitchen provides plenty of cabinet space and flows seamlessly into the dining area, creating the perfect space for everyday living and entertaining. Both bedrooms are generously sized, while the two full bathrooms have been thoughtfully updated for a clean, modern feel. Ample storage can be found throughout the home. Outside, enjoy the convenience of a deep covered carport, utility shed, and a peaceful setting on a desirable street within a welcoming golf community. Located just moments from shopping, restaurants, medical facilities, entertainment, and all the amenities The Villages has to give, you'll enjoy both convenience and a relaxed Florida lifestyle. With easy access to major highways and the Florida Turnpike, commuting is simple and efficient. No to mention, all the Villages activities are accessible and only a short golf car ride away! For outdoor enthusiasts, Serenity Pond is just a short stroll away, offering a tranquil spot for catch-and-release fishing and enjoying nature. Don't miss your chance to own this beautifully renovated home in a prime location. Schedule your private showing today!

116 Cypress Road, Wildwood
$119,900
2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
ANOTHER PRICE IMPROVEMENT!!! Welcome to this charming home offering nearly 1,300 square feet of comfortable living space, thoughtfully designed with an open floor plan perfect for both everyday living and entertaining. The spacious layout features a bright and airy living room and dining room combination, seamlessly flowing into a large, open kitchen with plenty of room for cooking, gathering, and storage. In addition to the main living areas, you’ll find a separate family room—ideal for relaxing, a home office, or a media space. The home sits on an oversized lot, providing exceptional privacy and plenty of outdoor space to enjoy. The entire outside of the home was recently painted. Recent updates add peace of mind and modern appeal, including a brand-new air conditioning system installed in February 2026 and a new water heater in March 2026. All the flooring was installed in 2024. The home also features new front windows, a new sliding glass door, newer appliances throughout. An oversized carport offers ample covered parking and additional storage space. With its combination of updates, space, and privacy, this home is a fantastic opportunity you won’t want to miss.The community is absolutely gorgeous with countless amenities, which include: large swimming pool with hot tub, 18 hole championship golf course, driving range and putting greens, shuffleboard, tennis, pickle ball, fitness center, library, billiards room, softball field, and a 5 star restaurant and lounge. What more can you ask for? This is a beautiful home in a beautiful community. You won't be disappointed!!!

108 N Timber Trail, Wildwood
$84,900
2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
By far the best value in Continental Country Club, located minutes from the Villages! This clean, functional, move-in ready home offers a fantastic opportunity to enjoy everything the retired lifestyle is known for—golf, recreation, entertainment, and an active 55+ community. While the home could benefit from some cosmetic updates, the price simply can’t be beat, making it the perfect opportunity to add your own personal touches and build instant value. The seller is also offering a $1,000 closing cost credit for buyers who close within 30 days of contract. Inside, you’ll find a spacious and inviting layout with a bright living room that flows into an air-conditioned Florida Room, creating additional space for relaxing or entertaining year-round. The main living areas feature luxury vinyl plank flooring, offering a clean, modern, and low-maintenance feel. The kitchen includes a convenient breakfast bar, while the dining area features a built-in hutch for extra storage and display. The primary suite offers a large walk-in closet and an en-suite bath with a walk-in shower. An attached workshop and carport add extra convenience and functionality. Living in Continental Country Club means enjoying a true resort-style lifestyle with access to an impressive list of amenities including an 18-hole championship golf course, clubhouse with restaurant and lounge, pool, tennis and pickleball courts, fitness center, library, billiards room, arts and crafts studios, a woodcrafter’s shop, and shuffleboard courts. Residents also enjoy access to Lake Okahumpka for boating, fishing from the dock, and on-site boat storage. The community is conveniently located just five minutes from The Villages with easy access to shopping, dining, entertainment, and medical services, and near I-75 and the Florida Turnpike, placing Orlando about an hour away and Tampa or Daytona Beach roughly 90 minutes away. Buyers must be 55+ with a minimum 700 credit score and complete a community application and credit check. This is an incredible opportunity to enjoy the Florida lifestyle in a well-maintained home with endless potential.

415 S Timber Trail, Wildwood
Start Your Search