Timberwoods Estates Homes with Community Mailbox Community Features

Timberwoods Estates Homes with Community Mailbox Community Features

Welcome to Timberwoods Estates, a picturesque subdivision nestled in the heart of Wildwood, Florida, within the charming Sumter County. This serene community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a peaceful lifestyle in sunny Florida.

Timberwoods Estates boasts a variety of beautifully designed homes that cater to diverse tastes and preferences. Each residence is thoughtfully crafted, featuring modern amenities and spacious layouts that create a warm and inviting atmosphere. Homeowners here enjoy the luxury of a community mailbox, fostering a sense of connection and community spirit among neighbors. This feature not only enhances convenience but also encourages friendly interactions, making it easier to build lasting relationships with those around you.

The community is surrounded by lush greenery and offers ample opportunities for outdoor activities. Residents can take leisurely strolls through the scenic streets, enjoy picnics in nearby parks, or explore the natural beauty of the surrounding area. With its close proximity to local shopping, dining, and recreational options, Timberwoods Estates provides everything you need just a stone’s throw away.

Whether you are looking for a place to settle down or a seasonal retreat, Timberwoods Estates is a hidden gem in Wildwood, Florida. Embrace a lifestyle of comfort and community in this charming subdivision, where your dream home awaits! Come and experience the warmth and hospitality that Timberwoods Estates has to offer – you won’t want to leave!

Newest Timberwoods Estates Homes with Community Mailbox Community Features

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

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Brian Scott Smith PA

Before launching his real estate career, Brian Smith spent over a decade in the construction industry, working hands-on with builders throughout Central Florida. That experience gave him an in-depth understanding of the homebuilding process—insight he now brings to his real estate clients, offering a level of expertise that sets him apart from most agents. In 2012, Brian joined his family’s firm, ERA Professional Realty. It was a “sink or swim” environment, and at the time, he wasn’t sure why his parents were so tough on him. Looking back, he’s grateful—they were preparing him for the challenges of a demanding industry, and that foundation shaped the dedicated, knowledgeable agent he is today. Since then, Brian has consistently ranked among the area’s top producers. His success is built on attention to detail, deep market knowledge, and a genuine commitment to client service. He stays current with real estate technology and prides himself on creating a smooth, informed experience for every buyer and seller. Brian has helped countless retirees transition to and from Florida, and he takes particular pride in assisting veterans and seniors through major life changes. In 2015, he was honored as REALTOR® of the Year at ERA Grizzard Real Estate. Today, he continues to list and sell millions of dollars in residential real estate annually and is expanding into commercial properties to serve an even broader range of client needs. A fifth-generation Floridian, Brian was born and raised in Central Florida. His local knowledge runs deep—something clients find to be a true asset when navigating the real estate market. Outside of work, Brian’s greatest pride is being a dad. He enjoys fishing with his son and watching his daughters grow into her own unique spirit. If you’re thinking about making a move, Brian Smith, REALTOR®, is a full-time agent ready to bring hard work, experience, and local expertise to your next real estate transaction.

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