Timberwoods Estates Homes with Trail(s) Amenities

Timberwoods Estates Homes with Trail(s) Amenities

Welcome to Timberwoods Estates, a hidden gem nestled in the heart of Wildwood, Florida, within the charming Sumter County. This picturesque subdivision offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and nature enthusiasts alike.

Timberwoods Estates boasts a collection of beautifully designed homes that cater to a variety of lifestyles. Each residence is thoughtfully constructed, featuring spacious layouts, contemporary finishes, and lush landscaping that enhances the overall appeal of this serene community. Whether you’re seeking a cozy retreat or a family-friendly abode, Timberwoods Estates has something for everyone.

One of the standout features of this delightful neighborhood is its extensive network of trails. Perfect for morning jogs, leisurely strolls, or evening bike rides, the trails wind through the scenic beauty of the area, allowing residents to immerse themselves in nature. These pathways not only promote a healthy lifestyle but also foster a sense of community as neighbors come together to enjoy the great outdoors.

In addition to its stunning homes and trails, Timberwoods Estates is conveniently located near a variety of shopping, dining, and recreational options. With easy access to major highways, commuting to nearby cities is a breeze, ensuring you can enjoy the best of both worlds – the peace of suburban living and the vibrancy of urban life.

Discover the charm of Timberwoods Estates, where your dream home awaits amidst the beauty of Wildwood, Florida. Come and experience the lifestyle you’ve always desired!

Newest Timberwoods Estates Homes with Trail(s) Amenities

705 Oak Boulevard, Wildwood
$238,900
3 Beds ⋅ 2 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
Welcome to 705 Oak Blvd, a spacious TURNKEY 3-bedroom, 2-bath home offering 1,680 sq. ft. of comfortable living in the sought-after Continental Country Club, a gated 55+ golf community just minutes from The Villages. Situated on a beautifully landscaped .22-acre lot, this inviting home features vaulted ceilings, a bright and spacious living area, inside laundry, and a well-equipped kitchen with appliances included. Enjoy Florida living from the enclosed porch, while the attached 2-car garage provides exceptional parking and storage—a feature not commonly found among many homes in the community. Continental Country Club offers an impressive active-adult lifestyle with a clubhouse, community pool, fitness center, dog park, tennis courts, restaurant, golf-cart-friendly streets, and an 18-hole championship golf course. The monthly association fee also includes cable TV, internet, trash, and grounds maintenance. Whether you're searching for a full-time residence or a seasonal Florida retreat, this move-in-ready home delivers the space, convenience, amenities, and lifestyle you've been looking for.

705 Oak Boulevard, Wildwood
802 Oak Boulevard, Wildwood
$189,900
2 Beds ⋅ 4 Baths ⋅ Timberwoods Estates SubDv. ⋅ 34785 Zip Code
Step into this exquisite waterfront sanctuary in Continental Country Club, where refined living meets serene natural beauty in a residence designed for comfort, sophistication, and effortless Florida living. This luxury-styled 2-bedroom, 2-bath home unfolds with an elegant, well-crafted floor plan that captures peaceful water views from the moment you enter. The family room becomes a private retreat overlooking the deck and pond—your front-row seat to the fountain, shimmering water, and daily wildlife. It’s the perfect setting for savoring your morning coffee or unwinding with an evening beverage while entertaining guests in style. The open kitchen offers lanai seating, barstools, and generous counter space, flowing seamlessly into a grand living room ideal for upscale gatherings. The primary suite is a calming haven with abundant closets, a beautifully appointed bath, and fresh paint throughout that enhances the home’s polished, high-end feel. Guests will enjoy their own luxurious retreat with an oversized bedroom and bath, plus inside laundry discreetly tucked behind custom barn doors for added charm and convenience. Downstairs, discover a full bonus living level—complete with an additional bedroom—perfect for hosting guests or transforming into a craft studio, workshop, or private lounge. The garage with full door access leads to a well-designed driveway framed by manicured landscaping and custom wood shutters that elevate the home’s curb appeal. Out back, a substantial dock invites you to embrace waterfront living at its finest—relaxing, fishing, or simply enjoying the peaceful setting. This exceptional property includes the Resident Owner Certificate, is priced for immediate interest, and delivers a rare blend of luxury, comfort and Florida Lifestyle. You'll want to call your agent quickly - THIS IS THE ONE!!

802 Oak Boulevard, Wildwood
413 S Timber Trail, Wildwood
$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
101 Cypress Road, Wildwood
$125,000
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
108 N Timber Trail, 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
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