Timberwoods Estates Homes with Gated Amenities

Timberwoods Estates Homes with Gated Amenities

Welcome to Timberwoods Estates, a hidden gem nestled in the heart of Wildwood, Florida, within the picturesque Sumter County. This exquisite subdivision offers a perfect blend of tranquility and modern living, ideal for families, retirees, and everyone in between.

Timberwoods Estates is renowned for its gated amenities, providing residents with a secure and serene environment to call home. The community is thoughtfully designed, featuring beautifully landscaped grounds, winding pathways, and vibrant green spaces that invite you to explore and enjoy the outdoors. The gated entrance not only enhances privacy but also fosters a sense of community among neighbors, making it easy to forge lasting friendships.

The homes in Timberwoods Estates are crafted with attention to detail, showcasing various architectural styles that cater to diverse tastes. Each residence is designed to maximize comfort and functionality, boasting spacious layouts, modern finishes, and ample natural light. Many homes feature private backyards, perfect for outdoor gatherings or simply relaxing under the Florida sun.

With convenient access to local amenities, including shopping, dining, and recreational activities, Timberwoods Estates offers the perfect balance of suburban tranquility and urban accessibility. Residents can enjoy nearby parks, golf courses, and nature trails, making it easy to embrace an active lifestyle.

If you're searching for a place that combines luxury, security, and a strong sense of community, Timberwoods Estates is the ideal choice. Discover your dream home in this charming subdivision and experience the best of Wildwood living today!

Newest Timberwoods Estates Homes with Gated Amenities

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

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

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

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

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

2 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code

PRICE DROP!! Seller moved!! It's ready for you and...YOU MUST GO TAKE A LOOK AT THIS HOME, IT HAS ALL YOU ARE LOOKING FOR! This fabulous 2-bed, 2-bath home offers an incredible amount of space and versatility, featuring an oversized workshop/shed and golf cart barn/garage YOU COULD PARK YOUR CAR IN IT TOO, along with a double driveway and double carport that allow parking for up to six vehicles plus room for boats, bikes, golf carts, and all your favorite toys. The home has been exceptionally well kept, with newer windows and flooring throughout, and an open, spacious floor plan that includes a formal dining area, an eat-in kitchen with abundant cabinetry, and even a front coat closet for those extra essentials. The primary bedroom boasts an impressively large en-suite bathroom and walk-in closet, while the guest bedroom and bath are also oversized with closets galore, and a built-in desk area provides a perfect workspace for anyone working from home. To top it all off, the expansive all-season Florida room offers endless possibilities — ideal for entertaining, relaxing, or even converting into a third bedroom if needed. Located in the wonderful Continental Country Club in Wildwood, just two minutes from The Villages, this community offers over 50 clubs, tennis, pickleball, a pool and hot tub, top-notch softball fields and teams, a great pub, formal dining, and so much more. Call your agent today and make this one YOUR HOME TODAY!!

805 Oak Boulevard, Wildwood

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